id	sid	tid	token	lemma	pos
eurjchem-1150	1	1	untitled	untitle	VERB
eurjchem-1150	1	2	european	european	PROPN
eurjchem-1150	1	3	journal	journal	PROPN
eurjchem-1150	1	4	of	of	ADP
eurjchem-1150	1	5	chemistry	chemistry	NOUN
eurjchem-1150	1	6	6	6	NUM
eurjchem-1150	1	7	(	(	PUNCT
eurjchem-1150	1	8	1	1	NUM
eurjchem-1150	1	9	)	)	PUNCT
eurjchem-1150	1	10	(	(	PUNCT
eurjchem-1150	1	11	2015	2015	NUM
eurjchem-1150	1	12	)	)	PUNCT
eurjchem-1150	1	13	93‐97	93‐97	NUM
eurjchem-1150	1	14	european	european	PROPN
eurjchem-1150	1	15	journal	journal	PROPN
eurjchem-1150	1	16	of	of	ADP
eurjchem-1150	1	17	chemistry	chemistry	NOUN
eurjchem-1150	1	18	issn	issn	PROPN
eurjchem-1150	1	19	2153‐2249	2153‐2249	PROPN
eurjchem-1150	1	20	(	(	PUNCT
eurjchem-1150	1	21	print	print	NOUN
eurjchem-1150	1	22	)	)	PUNCT
eurjchem-1150	1	23	/	/	SYM
eurjchem-1150	1	24	issn	issn	PROPN
eurjchem-1150	1	25	2153‐2257	2153‐2257	NUM
eurjchem-1150	1	26	(	(	PUNCT
eurjchem-1150	1	27	online	online	ADJ
eurjchem-1150	1	28	)	)	PUNCT
eurjchem-1150	1	29			NOUN
eurjchem-1150	1	30	2015	2015	NUM
eurjchem-1150	1	31	atlanta	atlanta	PROPN
eurjchem-1150	1	32	publishing	publishing	PROPN
eurjchem-1150	1	33	house	house	PROPN
eurjchem-1150	1	34	llc	llc	PROPN
eurjchem-1150	1	35	‐	‐	PUNCT
eurjchem-1150	1	36	all	all	DET
eurjchem-1150	1	37	rights	right	NOUN
eurjchem-1150	1	38	reserved	reserve	VERB
eurjchem-1150	1	39	‐	‐	NOUN
eurjchem-1150	1	40	printed	print	VERB
eurjchem-1150	1	41	in	in	ADP
eurjchem-1150	1	42	the	the	DET
eurjchem-1150	1	43	usa	usa	PROPN
eurjchem-1150	1	44	http://dx.doi.org/10.5155/eurjchem.6.1.93‐97.1150	http://dx.doi.org/10.5155/eurjchem.6.1.93‐97.1150	PROPN
eurjchem-1150	1	45	european	european	PROPN
eurjchem-1150	1	46	journal	journal	PROPN
eurjchem-1150	1	47	of	of	ADP
eurjchem-1150	1	48	chemistry	chemistry	PROPN
eurjchem-1150	1	49	journal	journal	PROPN
eurjchem-1150	1	50	webpage	webpage	NOUN
eurjchem-1150	1	51	:	:	PUNCT
eurjchem-1150	1	52	www.eurjchem.com	www.eurjchem.com	X
eurjchem-1150	1	53	stereoselective	stereoselective	ADJ
eurjchem-1150	1	54	total	total	ADJ
eurjchem-1150	1	55	synthesis	synthesis	NOUN
eurjchem-1150	1	56	of	of	ADP
eurjchem-1150	1	57	pectinolide	pectinolide	ADJ
eurjchem-1150	1	58	h	h	NOUN
eurjchem-1150	1	59	and	and	CCONJ
eurjchem-1150	1	60	4'‐epi‐pectinolide	4'‐epi‐pectinolide	PROPN
eurjchem-1150	1	61	h	h	PROPN
eurjchem-1150	1	62	ramesh	ramesh	PROPN
eurjchem-1150	1	63	perla	perla	PROPN
eurjchem-1150	1	64	and	and	CCONJ
eurjchem-1150	1	65	nitin	nitin	PROPN
eurjchem-1150	1	66	wasantrao	wasantrao	VERB
eurjchem-1150	1	67	fadnavis	fadnavis	PROPN
eurjchem-1150	1	68	*	*	PUNCT
eurjchem-1150	1	69	natural	natural	ADJ
eurjchem-1150	1	70	products	product	NOUN
eurjchem-1150	1	71	chemistry	chemistry	NOUN
eurjchem-1150	1	72	division	division	NOUN
eurjchem-1150	1	73	,	,	PUNCT
eurjchem-1150	1	74	indian	indian	PROPN
eurjchem-1150	1	75	institute	institute	PROPN
eurjchem-1150	1	76	of	of	ADP
eurjchem-1150	1	77	chemical	chemical	PROPN
eurjchem-1150	1	78	technology	technology	PROPN
eurjchem-1150	1	79	,	,	PUNCT
eurjchem-1150	1	80	habsiguda	habsiguda	NOUN
eurjchem-1150	1	81	,	,	PUNCT
eurjchem-1150	1	82	hyderabad‐500007	hyderabad‐500007	NOUN
eurjchem-1150	1	83	,	,	PUNCT
eurjchem-1150	1	84	india	india	PROPN
eurjchem-1150	1	85	*	*	PUNCT
eurjchem-1150	1	86	corresponding	correspond	VERB
eurjchem-1150	1	87	author	author	NOUN
eurjchem-1150	1	88	at	at	ADP
eurjchem-1150	1	89	:	:	PUNCT
eurjchem-1150	1	90	natural	natural	ADJ
eurjchem-1150	1	91	products	product	NOUN
eurjchem-1150	1	92	chemistry	chemistry	NOUN
eurjchem-1150	1	93	division	division	NOUN
eurjchem-1150	1	94	,	,	PUNCT
eurjchem-1150	1	95	indian	indian	PROPN
eurjchem-1150	1	96	institute	institute	PROPN
eurjchem-1150	1	97	of	of	ADP
eurjchem-1150	1	98	chemical	chemical	PROPN
eurjchem-1150	1	99	technology	technology	PROPN
eurjchem-1150	1	100	,	,	PUNCT
eurjchem-1150	1	101	habsiguda	habsiguda	NOUN
eurjchem-1150	1	102	,	,	PUNCT
eurjchem-1150	1	103	hyderabad‐500007	hyderabad‐500007	NOUN
eurjchem-1150	1	104	,	,	PUNCT
eurjchem-1150	1	105	india	india	PROPN
eurjchem-1150	1	106	.	.	PUNCT
eurjchem-1150	2	1	tel	tel	PROPN
eurjchem-1150	2	2	.	.	PUNCT
eurjchem-1150	2	3	:	:	PUNCT
eurjchem-1150	3	1	+91.40.27191631	+91.40.27191631	NUM
eurjchem-1150	3	2	.	.	PUNCT
eurjchem-1150	4	1	fax	fax	NOUN
eurjchem-1150	4	2	:	:	PUNCT
eurjchem-1150	4	3	+91.40.27160512	+91.40.27160512	PROPN
eurjchem-1150	4	4	.	.	PUNCT
eurjchem-1150	4	5	e‐mail	e‐mail	PUNCT
eurjchem-1150	5	1	address	address	NOUN
eurjchem-1150	5	2	:	:	PUNCT
eurjchem-1150	5	3	fadnavis@iict.res.in	fadnavis@iict.res.in	NOUN
eurjchem-1150	5	4	(	(	PUNCT
eurjchem-1150	5	5	n.w	n.w	PROPN
eurjchem-1150	5	6	.	.	PROPN
eurjchem-1150	5	7	fadnavis	fadnavis	PROPN
eurjchem-1150	5	8	)	)	PUNCT
eurjchem-1150	5	9	.	.	PUNCT
eurjchem-1150	6	1	article	article	NOUN
eurjchem-1150	6	2	information	information	PROPN
eurjchem-1150	6	3	abstract	abstract	ADJ
eurjchem-1150	6	4	doi	doi	NOUN
eurjchem-1150	6	5	:	:	PUNCT
eurjchem-1150	6	6	10.5155	10.5155	NUM
eurjchem-1150	6	7	/	/	SYM
eurjchem-1150	6	8	eurjchem.6.1.93‐97.1150	eurjchem.6.1.93‐97.1150	PROPN
eurjchem-1150	6	9	received	receive	VERB
eurjchem-1150	6	10	:	:	PUNCT
eurjchem-1150	6	11	11	11	NUM
eurjchem-1150	6	12	september	september	PROPN
eurjchem-1150	6	13	2014	2014	NUM
eurjchem-1150	6	14	received	receive	VERB
eurjchem-1150	6	15	in	in	ADP
eurjchem-1150	6	16	revised	revise	VERB
eurjchem-1150	6	17	form	form	NOUN
eurjchem-1150	6	18	:	:	PUNCT
eurjchem-1150	6	19	13	13	NUM
eurjchem-1150	6	20	october	october	NOUN
eurjchem-1150	6	21	2014	2014	NUM
eurjchem-1150	6	22	accepted	accept	VERB
eurjchem-1150	6	23	:	:	PUNCT
eurjchem-1150	6	24	18	18	NUM
eurjchem-1150	6	25	october	october	PROPN
eurjchem-1150	6	26	2014	2014	NUM
eurjchem-1150	6	27	published	publish	VERB
eurjchem-1150	6	28	online	online	ADV
eurjchem-1150	6	29	:	:	PUNCT
eurjchem-1150	6	30	31	31	NUM
eurjchem-1150	6	31	march	march	PROPN
eurjchem-1150	6	32	2015	2015	NUM
eurjchem-1150	6	33	printed	print	VERB
eurjchem-1150	6	34	:	:	PUNCT
eurjchem-1150	6	35	31	31	NUM
eurjchem-1150	6	36	march	march	PROPN
eurjchem-1150	6	37	2015	2015	NUM
eurjchem-1150	6	38	the	the	DET
eurjchem-1150	6	39	total	total	ADJ
eurjchem-1150	6	40	synthesis	synthesis	NOUN
eurjchem-1150	6	41	of	of	ADP
eurjchem-1150	6	42	pectinolide	pectinolide	ADJ
eurjchem-1150	6	43	h	h	NOUN
eurjchem-1150	6	44	and	and	CCONJ
eurjchem-1150	6	45	4'‐epi‐pectinolide	4'‐epi‐pectinolide	PROPN
eurjchem-1150	6	46	h	h	NOUN
eurjchem-1150	6	47	was	be	AUX
eurjchem-1150	6	48	accomplished	accomplish	VERB
eurjchem-1150	6	49	with	with	ADP
eurjchem-1150	6	50	27	27	NUM
eurjchem-1150	6	51	%	%	NOUN
eurjchem-1150	6	52	yield	yield	NOUN
eurjchem-1150	6	53	in	in	ADP
eurjchem-1150	6	54	nine	nine	NUM
eurjchem-1150	6	55	steps	step	NOUN
eurjchem-1150	6	56	from	from	ADP
eurjchem-1150	6	57	inexpensive	inexpensive	ADJ
eurjchem-1150	6	58	and	and	CCONJ
eurjchem-1150	6	59	commercially	commercially	ADV
eurjchem-1150	6	60	available	available	ADJ
eurjchem-1150	6	61	compound	compound	NOUN
eurjchem-1150	6	62	,	,	PUNCT
eurjchem-1150	6	63	(	(	PUNCT
eurjchem-1150	6	64	+	+	ADJ
eurjchem-1150	6	65	)	)	PUNCT
eurjchem-1150	6	66	‐diethyl	‐diethyl	NOUN
eurjchem-1150	6	67	tartrate	tartrate	NOUN
eurjchem-1150	6	68	(	(	PUNCT
eurjchem-1150	6	69	(	(	PUNCT
eurjchem-1150	6	70	+	+	ADJ
eurjchem-1150	6	71	)	)	PUNCT
eurjchem-1150	6	72	det	det	PROPN
eurjchem-1150	6	73	)	)	PUNCT
eurjchem-1150	6	74	)	)	PUNCT
eurjchem-1150	6	75	by	by	ADP
eurjchem-1150	6	76	employing	employ	VERB
eurjchem-1150	6	77	swern	swern	ADJ
eurjchem-1150	6	78	oxidation	oxidation	NOUN
eurjchem-1150	6	79	,	,	PUNCT
eurjchem-1150	6	80	wittig	wittig	NOUN
eurjchem-1150	6	81	olefination	olefination	NOUN
eurjchem-1150	6	82	,	,	PUNCT
eurjchem-1150	6	83	grignard	grignard	NOUN
eurjchem-1150	6	84	and	and	CCONJ
eurjchem-1150	6	85	lactonization	lactonization	NOUN
eurjchem-1150	6	86	reactions	reaction	NOUN
eurjchem-1150	6	87	.	.	PUNCT
eurjchem-1150	7	1	keywords	keyword	NOUN
eurjchem-1150	7	2	reduction	reduction	VERB
eurjchem-1150	7	3	pectinolide	pectinolide	ADJ
eurjchem-1150	7	4	h	h	PROPN
eurjchem-1150	7	5	lactonization	lactonization	PROPN
eurjchem-1150	7	6	swern	swern	ADJ
eurjchem-1150	7	7	oxidation	oxidation	NOUN
eurjchem-1150	7	8	wittig	wittig	NOUN
eurjchem-1150	7	9	olefination	olefination	NOUN
eurjchem-1150	7	10	grignard	grignard	NOUN
eurjchem-1150	7	11	reaction	reaction	NOUN
eurjchem-1150	7	12	cite	cite	VERB
eurjchem-1150	7	13	this	this	PRON
eurjchem-1150	7	14	:	:	PUNCT
eurjchem-1150	7	15	eur	eur	PROPN
eurjchem-1150	7	16	.	.	PUNCT
eurjchem-1150	8	1	j.	j.	PROPN
eurjchem-1150	8	2	chem	chem	PROPN
eurjchem-1150	8	3	.	.	PUNCT
eurjchem-1150	9	1	2015	2015	NUM
eurjchem-1150	9	2	,	,	PUNCT
eurjchem-1150	9	3	6(1	6(1	NUM
eurjchem-1150	9	4	)	)	PUNCT
eurjchem-1150	9	5	,	,	PUNCT
eurjchem-1150	9	6	93‐97	93‐97	NUM
eurjchem-1150	9	7	1	1	NUM
eurjchem-1150	9	8	.	.	PUNCT
eurjchem-1150	9	9	introduction	introduction	NOUN
eurjchem-1150	9	10	pectinolide	pectinolide	PROPN
eurjchem-1150	9	11	h	h	NOUN
eurjchem-1150	9	12	(	(	PUNCT
eurjchem-1150	9	13	1	1	NUM
eurjchem-1150	9	14	)	)	PUNCT
eurjchem-1150	9	15	(	(	PUNCT
eurjchem-1150	9	16	figure	figure	NOUN
eurjchem-1150	9	17	1	1	NUM
eurjchem-1150	9	18	)	)	PUNCT
eurjchem-1150	9	19	isolated	isolate	VERB
eurjchem-1150	9	20	from	from	ADP
eurjchem-1150	9	21	aerial	aerial	ADJ
eurjchem-1150	9	22	parts	part	NOUN
eurjchem-1150	9	23	of	of	ADP
eurjchem-1150	9	24	a	a	DET
eurjchem-1150	9	25	mexican	mexican	ADJ
eurjchem-1150	9	26	terrestrial	terrestrial	ADJ
eurjchem-1150	9	27	plant	plant	NOUN
eurjchem-1150	9	28	hyptis	hyptis	PROPN
eurjchem-1150	9	29	pectinata	pectinata	VERB
eurjchem-1150	9	30	displays	display	VERB
eurjchem-1150	9	31	significant	significant	ADJ
eurjchem-1150	9	32	antimicrobial	antimicrobial	ADJ
eurjchem-1150	9	33	activity	activity	NOUN
eurjchem-1150	9	34	against	against	ADP
eurjchem-1150	9	35	a	a	DET
eurjchem-1150	9	36	panel	panel	NOUN
eurjchem-1150	9	37	of	of	ADP
eurjchem-1150	9	38	multidrug‐resistant	multidrug‐resistant	ADJ
eurjchem-1150	9	39	strains	strain	NOUN
eurjchem-1150	9	40	of	of	ADP
eurjchem-1150	9	41	staphylococcus	staphylococcus	NOUN
eurjchem-1150	9	42	aureus	aureus	NOUN
eurjchem-1150	10	1	[	[	X
eurjchem-1150	10	2	1	1	NUM
eurjchem-1150	10	3	]	]	PUNCT
eurjchem-1150	10	4	.	.	PUNCT
eurjchem-1150	11	1	the	the	DET
eurjchem-1150	11	2	molecule	molecule	NOUN
eurjchem-1150	11	3	possesses	possess	VERB
eurjchem-1150	11	4	an	an	DET
eurjchem-1150	11	5	α	α	NOUN
eurjchem-1150	11	6	,	,	PUNCT
eurjchem-1150	11	7	β‐unsaturated	β‐unsaturated	PUNCT
eurjchem-1150	11	8	γ‐lactone	γ‐lactone	NOUN
eurjchem-1150	11	9	motif	motif	NOUN
eurjchem-1150	11	10	common	common	ADJ
eurjchem-1150	11	11	to	to	ADP
eurjchem-1150	11	12	many	many	ADJ
eurjchem-1150	11	13	natural	natural	ADJ
eurjchem-1150	11	14	products	product	NOUN
eurjchem-1150	11	15	exhibiting	exhibit	VERB
eurjchem-1150	11	16	antibacterial	antibacterial	ADJ
eurjchem-1150	11	17	and	and	CCONJ
eurjchem-1150	11	18	anti‐inflammatory	anti‐inflammatory	NOUN
eurjchem-1150	11	19	activities	activity	NOUN
eurjchem-1150	11	20	.	.	PUNCT
eurjchem-1150	12	1	many	many	ADJ
eurjchem-1150	12	2	compounds	compound	NOUN
eurjchem-1150	12	3	with	with	ADP
eurjchem-1150	12	4	similar	similar	ADJ
eurjchem-1150	12	5	structures	structure	NOUN
eurjchem-1150	12	6	have	have	AUX
eurjchem-1150	12	7	also	also	ADV
eurjchem-1150	12	8	been	be	AUX
eurjchem-1150	12	9	reported	report	VERB
eurjchem-1150	12	10	to	to	PART
eurjchem-1150	12	11	be	be	AUX
eurjchem-1150	12	12	potentially	potentially	ADV
eurjchem-1150	12	13	useful	useful	ADJ
eurjchem-1150	12	14	as	as	ADP
eurjchem-1150	12	15	anticancer	anticancer	NOUN
eurjchem-1150	12	16	agents	agent	NOUN
eurjchem-1150	12	17	and	and	CCONJ
eurjchem-1150	12	18	enzyme	enzyme	VERB
eurjchem-1150	12	19	inhibitors	inhibitor	NOUN
eurjchem-1150	12	20	[	[	X
eurjchem-1150	12	21	2‐10	2‐10	X
eurjchem-1150	12	22	]	]	X
eurjchem-1150	12	23	.	.	PUNCT
eurjchem-1150	13	1	considering	consider	VERB
eurjchem-1150	13	2	the	the	DET
eurjchem-1150	13	3	importance	importance	NOUN
eurjchem-1150	13	4	of	of	ADP
eurjchem-1150	13	5	new	new	ADJ
eurjchem-1150	13	6	antimicrobial	antimicrobial	ADJ
eurjchem-1150	13	7	agents	agent	NOUN
eurjchem-1150	13	8	for	for	ADP
eurjchem-1150	13	9	multidrug	multidrug	VERB
eurjchem-1150	13	10	resistant	resistant	ADJ
eurjchem-1150	13	11	microorganisms	microorganism	NOUN
eurjchem-1150	13	12	,	,	PUNCT
eurjchem-1150	13	13	synthesis	synthesis	NOUN
eurjchem-1150	13	14	of	of	ADP
eurjchem-1150	13	15	molecules	molecule	NOUN
eurjchem-1150	13	16	such	such	ADJ
eurjchem-1150	13	17	as	as	ADP
eurjchem-1150	13	18	pectinolide	pectinolide	ADJ
eurjchem-1150	13	19	h	h	NOUN
eurjchem-1150	13	20	in	in	ADP
eurjchem-1150	13	21	a	a	DET
eurjchem-1150	13	22	simple	simple	ADJ
eurjchem-1150	13	23	and	and	CCONJ
eurjchem-1150	13	24	straightforward	straightforward	ADJ
eurjchem-1150	13	25	manner	manner	NOUN
eurjchem-1150	13	26	is	be	AUX
eurjchem-1150	13	27	necessary	necessary	ADJ
eurjchem-1150	13	28	.	.	PUNCT
eurjchem-1150	14	1	to	to	ADP
eurjchem-1150	14	2	the	the	DET
eurjchem-1150	14	3	best	good	ADJ
eurjchem-1150	14	4	of	of	ADP
eurjchem-1150	14	5	our	our	PRON
eurjchem-1150	14	6	knowledge	knowledge	NOUN
eurjchem-1150	14	7	,	,	PUNCT
eurjchem-1150	14	8	two	two	NUM
eurjchem-1150	14	9	reports	report	NOUN
eurjchem-1150	14	10	exist	exist	VERB
eurjchem-1150	14	11	for	for	ADP
eurjchem-1150	14	12	the	the	DET
eurjchem-1150	14	13	synthesis	synthesis	NOUN
eurjchem-1150	14	14	of	of	ADP
eurjchem-1150	14	15	pectinolide	pectinolide	ADJ
eurjchem-1150	14	16	h	h	NOUN
eurjchem-1150	14	17	(	(	PUNCT
eurjchem-1150	14	18	1	1	NUM
eurjchem-1150	14	19	)	)	PUNCT
eurjchem-1150	15	1	[	[	X
eurjchem-1150	15	2	11,12	11,12	NUM
eurjchem-1150	15	3	]	]	PUNCT
eurjchem-1150	15	4	.	.	PUNCT
eurjchem-1150	16	1	herein	herein	NOUN
eurjchem-1150	16	2	,	,	PUNCT
eurjchem-1150	16	3	we	we	PRON
eurjchem-1150	16	4	report	report	VERB
eurjchem-1150	16	5	an	an	DET
eurjchem-1150	16	6	easy	easy	ADJ
eurjchem-1150	16	7	approach	approach	NOUN
eurjchem-1150	16	8	to	to	PART
eurjchem-1150	16	9	compound	compound	VERB
eurjchem-1150	16	10	1	1	NUM
eurjchem-1150	16	11	carried	carry	VERB
eurjchem-1150	16	12	out	out	ADP
eurjchem-1150	16	13	in	in	ADP
eurjchem-1150	16	14	nine	nine	NUM
eurjchem-1150	16	15	simple	simple	ADJ
eurjchem-1150	16	16	steps	step	NOUN
eurjchem-1150	16	17	.	.	PUNCT
eurjchem-1150	17	1	our	our	PRON
eurjchem-1150	17	2	synthetic	synthetic	ADJ
eurjchem-1150	17	3	strategy	strategy	NOUN
eurjchem-1150	17	4	also	also	ADV
eurjchem-1150	17	5	provides	provide	VERB
eurjchem-1150	17	6	the	the	DET
eurjchem-1150	17	7	epimer	epimer	NOUN
eurjchem-1150	17	8	4'‐epi‐	4'‐epi‐	NUM
eurjchem-1150	17	9	pectinolide	pectinolide	ADJ
eurjchem-1150	17	10	h	h	NOUN
eurjchem-1150	17	11	(	(	PUNCT
eurjchem-1150	17	12	2	2	NUM
eurjchem-1150	17	13	)	)	PUNCT
eurjchem-1150	17	14	.	.	PUNCT
eurjchem-1150	18	1	2	2	X
eurjchem-1150	18	2	.	.	X
eurjchem-1150	18	3	experimental	experimental	ADJ
eurjchem-1150	18	4	all	all	DET
eurjchem-1150	18	5	commercially	commercially	ADV
eurjchem-1150	18	6	available	available	ADJ
eurjchem-1150	18	7	chemicals	chemical	NOUN
eurjchem-1150	18	8	were	be	AUX
eurjchem-1150	18	9	purchased	purchase	VERB
eurjchem-1150	18	10	from	from	ADP
eurjchem-1150	18	11	sigma	sigma	PROPN
eurjchem-1150	18	12	aldrich	aldrich	PROPN
eurjchem-1150	18	13	and	and	CCONJ
eurjchem-1150	18	14	used	use	VERB
eurjchem-1150	18	15	without	without	ADP
eurjchem-1150	18	16	purification	purification	NOUN
eurjchem-1150	18	17	.	.	PUNCT
eurjchem-1150	19	1	all	all	DET
eurjchem-1150	19	2	experiments	experiment	NOUN
eurjchem-1150	19	3	were	be	AUX
eurjchem-1150	19	4	carried	carry	VERB
eurjchem-1150	19	5	out	out	ADP
eurjchem-1150	19	6	under	under	ADP
eurjchem-1150	19	7	an	an	DET
eurjchem-1150	19	8	inert	inert	ADJ
eurjchem-1150	19	9	nitrogen	nitrogen	NOUN
eurjchem-1150	19	10	atmosphere	atmosphere	NOUN
eurjchem-1150	19	11	.	.	PUNCT
eurjchem-1150	20	1	2.1	2.1	NUM
eurjchem-1150	20	2	.	.	PUNCT
eurjchem-1150	20	3	instrumentation	instrumentation	NOUN
eurjchem-1150	20	4	1h	1h	NUM
eurjchem-1150	20	5	and	and	CCONJ
eurjchem-1150	20	6	13c	13c	NOUN
eurjchem-1150	20	7	nmr	nmr	NOUN
eurjchem-1150	20	8	spectra	spectra	NOUN
eurjchem-1150	20	9	were	be	AUX
eurjchem-1150	20	10	recorded	record	VERB
eurjchem-1150	20	11	on	on	ADP
eurjchem-1150	20	12	bruker	bruker	PROPN
eurjchem-1150	20	13	avance	avance	PROPN
eurjchem-1150	20	14	300	300	NUM
eurjchem-1150	20	15	mhz	mhz	NOUN
eurjchem-1150	20	16	and	and	CCONJ
eurjchem-1150	20	17	bruker	bruker	ADJ
eurjchem-1150	20	18	avance	avance	NOUN
eurjchem-1150	20	19	75	75	NUM
eurjchem-1150	20	20	mhz	mhz	NOUN
eurjchem-1150	20	21	spectrometers	spectrometer	NOUN
eurjchem-1150	20	22	,	,	PUNCT
eurjchem-1150	20	23	respect‐	respect‐	VERB
eurjchem-1150	20	24	tively	tively	ADV
eurjchem-1150	20	25	,	,	PUNCT
eurjchem-1150	20	26	using	use	VERB
eurjchem-1150	20	27	cdcl3	cdcl3	NOUN
eurjchem-1150	20	28	as	as	ADP
eurjchem-1150	20	29	solvent	solvent	NOUN
eurjchem-1150	20	30	and	and	CCONJ
eurjchem-1150	20	31	sime4	sime4	NOUN
eurjchem-1150	20	32	as	as	ADP
eurjchem-1150	20	33	the	the	DET
eurjchem-1150	20	34	internal	internal	ADJ
eurjchem-1150	20	35	standard	standard	NOUN
eurjchem-1150	20	36	.	.	PUNCT
eurjchem-1150	21	1	ft‐ir	ft‐ir	NOUN
eurjchem-1150	21	2	analyses	analysis	NOUN
eurjchem-1150	21	3	were	be	AUX
eurjchem-1150	21	4	performed	perform	VERB
eurjchem-1150	21	5	using	use	VERB
eurjchem-1150	21	6	perkin	perkin	PROPN
eurjchem-1150	21	7	elmer	elmer	PROPN
eurjchem-1150	21	8	rx1	rx1	PROPN
eurjchem-1150	21	9	ft‐ir	ft‐ir	NOUN
eurjchem-1150	21	10	spectrophotometer	spectrophotometer	NOUN
eurjchem-1150	21	11	.	.	PUNCT
eurjchem-1150	22	1	mass	mass	PROPN
eurjchem-1150	22	2	spectra	spectra	PROPN
eurjchem-1150	22	3	analyses	analysis	NOUN
eurjchem-1150	22	4	were	be	AUX
eurjchem-1150	22	5	performed	perform	VERB
eurjchem-1150	22	6	on	on	ADP
eurjchem-1150	22	7	vg	vg	ADP
eurjchem-1150	22	8	auto	auto	NOUN
eurjchem-1150	22	9	spec	spec	NOUN
eurjchem-1150	22	10	instrument	instrument	NOUN
eurjchem-1150	22	11	.	.	PUNCT
eurjchem-1150	23	1	optical	optical	ADJ
eurjchem-1150	23	2	rotations	rotation	NOUN
eurjchem-1150	23	3	were	be	AUX
eurjchem-1150	23	4	determined	determine	VERB
eurjchem-1150	23	5	using	use	VERB
eurjchem-1150	23	6	jasco	jasco	PROPN
eurjchem-1150	23	7	dip	dip	NOUN
eurjchem-1150	23	8	360	360	NUM
eurjchem-1150	23	9	digital	digital	ADJ
eurjchem-1150	23	10	polarimeter	polarimeter	NOUN
eurjchem-1150	23	11	.	.	PUNCT
eurjchem-1150	24	1	2.2	2.2	NUM
eurjchem-1150	24	2	.	.	PUNCT
eurjchem-1150	24	3	synthesis	synthesis	NOUN
eurjchem-1150	24	4	2.2.1	2.2.1	NUM
eurjchem-1150	24	5	.	.	PUNCT
eurjchem-1150	24	6	synthesis	synthesis	NOUN
eurjchem-1150	24	7	of	of	ADP
eurjchem-1150	24	8	diethyl	diethyl	NOUN
eurjchem-1150	24	9	(	(	PUNCT
eurjchem-1150	24	10	4r,5r)‐2,2‐dimethyl‐1,3‐	4r,5r)‐2,2‐dimethyl‐1,3‐	NUM
eurjchem-1150	24	11	dioxolane‐4,5‐dicarboxylate	dioxolane‐4,5‐dicarboxylate	ADJ
eurjchem-1150	24	12	(	(	PUNCT
eurjchem-1150	24	13	7	7	NUM
eurjchem-1150	24	14	)	)	PUNCT
eurjchem-1150	24	15	a	a	DET
eurjchem-1150	24	16	solution	solution	NOUN
eurjchem-1150	24	17	of	of	ADP
eurjchem-1150	24	18	compound	compound	NOUN
eurjchem-1150	24	19	6	6	NUM
eurjchem-1150	24	20	(	(	PUNCT
eurjchem-1150	24	21	10	10	NUM
eurjchem-1150	24	22	g	g	NOUN
eurjchem-1150	24	23	,	,	PUNCT
eurjchem-1150	24	24	48.54	48.54	NUM
eurjchem-1150	24	25	mmol	mmol	NOUN
eurjchem-1150	24	26	)	)	PUNCT
eurjchem-1150	24	27	,	,	PUNCT
eurjchem-1150	24	28	p‐toluene	p‐toluene	SYM
eurjchem-1150	24	29	sulfonic	sulfonic	ADJ
eurjchem-1150	24	30	acid	acid	NOUN
eurjchem-1150	24	31	(	(	PUNCT
eurjchem-1150	24	32	100	100	NUM
eurjchem-1150	24	33	mg	mg	NOUN
eurjchem-1150	24	34	)	)	PUNCT
eurjchem-1150	24	35	in	in	ADP
eurjchem-1150	24	36	ch2cl2	ch2cl2	X
eurjchem-1150	24	37	(	(	PUNCT
eurjchem-1150	24	38	100	100	NUM
eurjchem-1150	24	39	ml	ml	NOUN
eurjchem-1150	24	40	)	)	PUNCT
eurjchem-1150	24	41	and	and	CCONJ
eurjchem-1150	24	42	2,2‐	2,2‐	NUM
eurjchem-1150	24	43	dimethoxypropane	dimethoxypropane	NOUN
eurjchem-1150	24	44	(	(	PUNCT
eurjchem-1150	24	45	12	12	NUM
eurjchem-1150	24	46	ml	ml	NOUN
eurjchem-1150	24	47	,	,	PUNCT
eurjchem-1150	24	48	97	97	NUM
eurjchem-1150	24	49	mmol	mmol	NOUN
eurjchem-1150	24	50	)	)	PUNCT
eurjchem-1150	24	51	was	be	AUX
eurjchem-1150	24	52	stirred	stir	VERB
eurjchem-1150	24	53	at	at	ADP
eurjchem-1150	24	54	room	room	NOUN
eurjchem-1150	24	55	temperature	temperature	NOUN
eurjchem-1150	24	56	for	for	ADP
eurjchem-1150	24	57	4	4	NUM
eurjchem-1150	24	58	h.	h.	NOUN
eurjchem-1150	24	59	the	the	DET
eurjchem-1150	24	60	reaction	reaction	NOUN
eurjchem-1150	24	61	mixture	mixture	NOUN
eurjchem-1150	24	62	was	be	AUX
eurjchem-1150	24	63	quenched	quench	VERB
eurjchem-1150	24	64	with	with	ADP
eurjchem-1150	24	65	solid	solid	ADJ
eurjchem-1150	24	66	nahco3	nahco3	NOUN
eurjchem-1150	24	67	,	,	PUNCT
eurjchem-1150	24	68	filtered	filter	VERB
eurjchem-1150	24	69	,	,	PUNCT
eurjchem-1150	24	70	solvent	solvent	NOUN
eurjchem-1150	24	71	was	be	AUX
eurjchem-1150	24	72	evaporated	evaporate	VERB
eurjchem-1150	24	73	under	under	ADP
eurjchem-1150	24	74	vacuum	vacuum	NOUN
eurjchem-1150	24	75	.	.	PUNCT
eurjchem-1150	25	1	the	the	DET
eurjchem-1150	25	2	crude	crude	ADJ
eurjchem-1150	25	3	product	product	NOUN
eurjchem-1150	25	4	was	be	AUX
eurjchem-1150	25	5	purified	purify	VERB
eurjchem-1150	25	6	by	by	ADP
eurjchem-1150	25	7	flash	flash	NOUN
eurjchem-1150	25	8	column	column	NOUN
eurjchem-1150	25	9	chroma‐	chroma‐	NUM
eurjchem-1150	25	10	tography	tography	NOUN
eurjchem-1150	25	11	(	(	PUNCT
eurjchem-1150	25	12	hexane	hexane	NOUN
eurjchem-1150	25	13	:	:	PUNCT
eurjchem-1150	25	14	etoac	etoac	ADJ
eurjchem-1150	25	15	,	,	PUNCT
eurjchem-1150	25	16	98:2	98:2	NUM
eurjchem-1150	25	17	,	,	PUNCT
eurjchem-1150	25	18	v	v	NOUN
eurjchem-1150	25	19	:	:	SYM
eurjchem-1150	25	20	v	v	NOUN
eurjchem-1150	25	21	)	)	PUNCT
eurjchem-1150	25	22	to	to	PART
eurjchem-1150	25	23	give	give	VERB
eurjchem-1150	25	24	compound	compound	NOUN
eurjchem-1150	25	25	7	7	NUM
eurjchem-1150	25	26	.	.	PUNCT
eurjchem-1150	26	1	color	color	NOUN
eurjchem-1150	26	2	:	:	PUNCT
eurjchem-1150	26	3	colorless	colorless	ADJ
eurjchem-1150	26	4	liquid	liquid	NOUN
eurjchem-1150	26	5	.	.	PUNCT
eurjchem-1150	27	1	yield	yield	NOUN
eurjchem-1150	27	2	:	:	PUNCT
eurjchem-1150	27	3	10.75	10.75	NUM
eurjchem-1150	27	4	g	g	NOUN
eurjchem-1150	27	5	,	,	PUNCT
eurjchem-1150	27	6	90	90	NUM
eurjchem-1150	27	7	%	%	NOUN
eurjchem-1150	27	8	.	.	PUNCT
eurjchem-1150	28	1	ft‐ir	ft‐ir	NOUN
eurjchem-1150	28	2	(	(	PUNCT
eurjchem-1150	28	3	neat	neat	ADJ
eurjchem-1150	28	4	,	,	PUNCT
eurjchem-1150	28	5	ν	ν	NOUN
eurjchem-1150	28	6	,	,	PUNCT
eurjchem-1150	28	7	cm‐1	cm‐1	PROPN
eurjchem-1150	28	8	):	):	PUNCT
eurjchem-1150	28	9	2990	2990	NUM
eurjchem-1150	28	10	,	,	PUNCT
eurjchem-1150	28	11	1753	1753	NUM
eurjchem-1150	28	12	,	,	PUNCT
eurjchem-1150	28	13	1216	1216	NUM
eurjchem-1150	28	14	.	.	PUNCT
eurjchem-1150	29	1	1h	1h	NUM
eurjchem-1150	29	2	nmr	nmr	NOUN
eurjchem-1150	29	3	(	(	PUNCT
eurjchem-1150	29	4	300	300	NUM
eurjchem-1150	29	5	mhz	mhz	NOUN
eurjchem-1150	29	6	,	,	PUNCT
eurjchem-1150	29	7	cdcl3	cdcl3	PROPN
eurjchem-1150	29	8	,	,	PUNCT
eurjchem-1150	29	9	δ	δ	PROPN
eurjchem-1150	29	10	,	,	PUNCT
eurjchem-1150	29	11	ppm	ppm	NOUN
eurjchem-1150	29	12	):	):	PUNCT
eurjchem-1150	29	13	1.31	1.31	NUM
eurjchem-1150	29	14	(	(	PUNCT
eurjchem-1150	29	15	t	t	PROPN
eurjchem-1150	29	16	,	,	PUNCT
eurjchem-1150	29	17	6h	6h	NUM
eurjchem-1150	29	18	,	,	PUNCT
eurjchem-1150	29	19	ch3‐ch2‐o	ch3‐ch2‐o	NOUN
eurjchem-1150	29	20	)	)	PUNCT
eurjchem-1150	29	21	,	,	PUNCT
eurjchem-1150	29	22	1.50	1.50	NUM
eurjchem-1150	29	23	(	(	PUNCT
eurjchem-1150	29	24	s	s	PROPN
eurjchem-1150	29	25	,	,	PUNCT
eurjchem-1150	29	26	6h	6h	NUM
eurjchem-1150	29	27	,	,	PUNCT
eurjchem-1150	29	28	(	(	PUNCT
eurjchem-1150	29	29	ch3)2c	ch3)2c	PROPN
eurjchem-1150	29	30	)	)	PUNCT
eurjchem-1150	29	31	,	,	PUNCT
eurjchem-1150	29	32	4.27	4.27	NUM
eurjchem-1150	29	33	(	(	PUNCT
eurjchem-1150	29	34	q	q	NOUN
eurjchem-1150	29	35	,	,	PUNCT
eurjchem-1150	29	36	4h	4h	NUM
eurjchem-1150	29	37	,	,	PUNCT
eurjchem-1150	29	38	ch2‐oco	ch2‐oco	PROPN
eurjchem-1150	29	39	)	)	PUNCT
eurjchem-1150	29	40	,	,	PUNCT
eurjchem-1150	29	41	4.76	4.76	NUM
eurjchem-1150	29	42	(	(	PUNCT
eurjchem-1150	29	43	s	s	PROPN
eurjchem-1150	29	44	,	,	PUNCT
eurjchem-1150	29	45	2h	2h	NUM
eurjchem-1150	29	46	,	,	PUNCT
eurjchem-1150	29	47	ch‐coo	ch‐coo	NOUN
eurjchem-1150	29	48	)	)	PUNCT
eurjchem-1150	29	49	.	.	PUNCT
eurjchem-1150	30	1	94	94	NUM
eurjchem-1150	30	2	perla	perla	NOUN
eurjchem-1150	30	3	and	and	CCONJ
eurjchem-1150	30	4	fadnavis	fadnavis	NOUN
eurjchem-1150	30	5	/	/	SYM
eurjchem-1150	30	6	european	european	PROPN
eurjchem-1150	30	7	journal	journal	PROPN
eurjchem-1150	30	8	of	of	ADP
eurjchem-1150	30	9	chemistry	chemistry	NOUN
eurjchem-1150	30	10	6	6	NUM
eurjchem-1150	30	11	(	(	PUNCT
eurjchem-1150	30	12	1	1	NUM
eurjchem-1150	30	13	)	)	PUNCT
eurjchem-1150	30	14	(	(	PUNCT
eurjchem-1150	30	15	2015	2015	NUM
eurjchem-1150	30	16	)	)	PUNCT
eurjchem-1150	30	17	93‐97	93‐97	NUM
eurjchem-1150	30	18	figure	figure	NOUN
eurjchem-1150	30	19	1	1	NUM
eurjchem-1150	30	20	.	.	PUNCT
eurjchem-1150	30	21	structure	structure	NOUN
eurjchem-1150	30	22	of	of	ADP
eurjchem-1150	30	23	pectinolide	pectinolide	ADJ
eurjchem-1150	30	24	a‐c	a‐c	PROPN
eurjchem-1150	30	25	,	,	PUNCT
eurjchem-1150	30	26	h	h	NOUN
eurjchem-1150	30	27	and	and	CCONJ
eurjchem-1150	30	28	4‐epi‐pectinolide	4‐epi‐pectinolide	NUM
eurjchem-1150	30	29	h.	h.	PROPN
eurjchem-1150	30	30	eto	eto	PROPN
eurjchem-1150	31	1	oet	oet	VERB
eurjchem-1150	32	1	o	o	NOUN
eurjchem-1150	33	1	o	o	X
eurjchem-1150	33	2	o	o	X
eurjchem-1150	33	3	o	o	X
eurjchem-1150	33	4	(	(	PUNCT
eurjchem-1150	33	5	+	+	NOUN
eurjchem-1150	33	6	)	)	PUNCT
eurjchem-1150	33	7	-det	-det	NOUN
eurjchem-1150	33	8	ho	ho	PROPN
eurjchem-1150	34	1	oh	oh	INTJ
eurjchem-1150	34	2	o	o	INTJ
eurjchem-1150	35	1	o	o	INTJ
eurjchem-1150	35	2	tbdpso	tbdpso	NOUN
eurjchem-1150	36	1	oh	oh	INTJ
eurjchem-1150	36	2	o	o	INTJ
eurjchem-1150	36	3	o	o	INTJ
eurjchem-1150	36	4	ro	ro	INTJ
eurjchem-1150	37	1	o	o	NOUN
eurjchem-1150	37	2	o	o	INTJ
eurjchem-1150	37	3	oet	oet	INTJ
eurjchem-1150	37	4	o	o	INTJ
eurjchem-1150	37	5	ro	ro	X
eurjchem-1150	38	1	o	o	NOUN
eurjchem-1150	38	2	o	o	X
eurjchem-1150	39	1	+	+	CCONJ
eurjchem-1150	39	2	o	o	INTJ
eurjchem-1150	39	3	oet	oet	INTJ
eurjchem-1150	39	4	ro	ro	INTJ
eurjchem-1150	40	1	o	o	NOUN
eurjchem-1150	41	1	o	o	X
eurjchem-1150	42	1	o	o	X
eurjchem-1150	42	2	h	h	NOUN
eurjchem-1150	43	1	ro	ro	NOUN
eurjchem-1150	44	1	o	o	INTJ
eurjchem-1150	44	2	o	o	INTJ
eurjchem-1150	45	1	oh	oh	INTJ
eurjchem-1150	45	2	ro	ro	INTJ
eurjchem-1150	45	3	o	o	X
eurjchem-1150	45	4	o	o	X
eurjchem-1150	45	5	oac	oac	VERB
eurjchem-1150	45	6	ho	ho	PROPN
eurjchem-1150	45	7	o	o	X
eurjchem-1150	45	8	o	o	X
eurjchem-1150	46	1	oac	oac	VERB
eurjchem-1150	47	1	o	o	NOUN
eurjchem-1150	47	2	o	o	X
eurjchem-1150	47	3	oac	oac	VERB
eurjchem-1150	47	4	o	o	X
eurjchem-1150	47	5	eto	eto	PROPN
eurjchem-1150	48	1	oh	oh	INTJ
eurjchem-1150	48	2	o	o	INTJ
eurjchem-1150	48	3	oac	oac	INTJ
eurjchem-1150	48	4	o	o	NOUN
eurjchem-1150	49	1	oh	oh	INTJ
eurjchem-1150	49	2	o	o	INTJ
eurjchem-1150	49	3	oac	oac	VERB
eurjchem-1150	49	4	o	o	NOUN
eurjchem-1150	50	1	+	+	CCONJ
eurjchem-1150	50	2	a	a	DET
eurjchem-1150	50	3	b	b	NOUN
eurjchem-1150	50	4	c	c	NOUN
eurjchem-1150	50	5	d	d	X
eurjchem-1150	50	6	e	e	X
eurjchem-1150	50	7	f	f	PROPN
eurjchem-1150	50	8	g	g	PROPN
eurjchem-1150	50	9	h	h	NOUN
eurjchem-1150	51	1	i	i	INTJ
eurjchem-1150	51	2	j	j	PROPN
eurjchem-1150	52	1	r	r	NOUN
eurjchem-1150	52	2	=	=	NOUN
eurjchem-1150	52	3	tbdps	tbdps	NOUN
eurjchem-1150	52	4	6	6	NUM
eurjchem-1150	52	5	7	7	NUM
eurjchem-1150	52	6	8	8	NUM
eurjchem-1150	52	7	9	9	NUM
eurjchem-1150	52	8	10a	10a	NOUN
eurjchem-1150	52	9	10b	10b	NOUN
eurjchem-1150	52	10	11	11	NUM
eurjchem-1150	52	11	12	12	NUM
eurjchem-1150	52	12	13	13	NUM
eurjchem-1150	52	13	14	14	NUM
eurjchem-1150	52	14	15	15	NUM
eurjchem-1150	52	15	1	1	NUM
eurjchem-1150	52	16	2	2	NUM
eurjchem-1150	52	17	10a:10b	10a:10b	NUM
eurjchem-1150	52	18	=	=	SYM
eurjchem-1150	52	19	80:20	80:20	NUM
eurjchem-1150	52	20	reagents	reagent	NOUN
eurjchem-1150	52	21	and	and	CCONJ
eurjchem-1150	52	22	conditions	condition	NOUN
eurjchem-1150	52	23	:	:	PUNCT
eurjchem-1150	52	24	a	a	X
eurjchem-1150	52	25	)	)	PUNCT
eurjchem-1150	52	26	2,2‐dmp	2,2‐dmp	NOUN
eurjchem-1150	52	27	,	,	PUNCT
eurjchem-1150	52	28	ptsa(cat	ptsa(cat	NOUN
eurjchem-1150	52	29	.	.	PUNCT
eurjchem-1150	52	30	)	)	PUNCT
eurjchem-1150	53	1	ch2cl2	ch2cl2	PROPN
eurjchem-1150	53	2	,	,	PUNCT
eurjchem-1150	53	3	rt	rt	PROPN
eurjchem-1150	53	4	,	,	PUNCT
eurjchem-1150	53	5	4	4	NUM
eurjchem-1150	53	6	h	h	NOUN
eurjchem-1150	53	7	,	,	PUNCT
eurjchem-1150	53	8	90	90	NUM
eurjchem-1150	53	9	%	%	NOUN
eurjchem-1150	53	10	.	.	PUNCT
eurjchem-1150	54	1	b	b	X
eurjchem-1150	54	2	)	)	PUNCT
eurjchem-1150	54	3	lialh4	lialh4	NOUN
eurjchem-1150	54	4	,	,	PUNCT
eurjchem-1150	54	5	thf	thf	NOUN
eurjchem-1150	54	6	,	,	PUNCT
eurjchem-1150	54	7	0	0	NUM
eurjchem-1150	55	1	°	°	ADP
eurjchem-1150	55	2	c	c	NOUN
eurjchem-1150	55	3	to	to	PART
eurjchem-1150	55	4	rt	rt	PROPN
eurjchem-1150	55	5	,	,	PUNCT
eurjchem-1150	55	6	1	1	NUM
eurjchem-1150	55	7	h	h	NOUN
eurjchem-1150	55	8	,	,	PUNCT
eurjchem-1150	55	9	85	85	NUM
eurjchem-1150	55	10	%	%	NOUN
eurjchem-1150	55	11	.	.	PUNCT
eurjchem-1150	56	1	c	c	X
eurjchem-1150	56	2	)	)	PUNCT
eurjchem-1150	56	3	tbdpscl	tbdpscl	NOUN
eurjchem-1150	56	4	,	,	PUNCT
eurjchem-1150	56	5	nah	nah	INTJ
eurjchem-1150	56	6	,	,	PUNCT
eurjchem-1150	56	7	thf	thf	NOUN
eurjchem-1150	56	8	,	,	PUNCT
eurjchem-1150	56	9	0	0	NUM
eurjchem-1150	57	1	°	°	ADP
eurjchem-1150	57	2	c	c	NOUN
eurjchem-1150	57	3	to	to	PART
eurjchem-1150	57	4	rt	rt	PROPN
eurjchem-1150	57	5	,	,	PUNCT
eurjchem-1150	57	6	2h	2h	NUM
eurjchem-1150	57	7	,	,	PUNCT
eurjchem-1150	57	8	90	90	NUM
eurjchem-1150	57	9	%	%	NOUN
eurjchem-1150	57	10	.	.	PUNCT
eurjchem-1150	58	1	d	d	X
eurjchem-1150	58	2	)	)	PUNCT
eurjchem-1150	58	3	(	(	PUNCT
eurjchem-1150	58	4	i	i	NOUN
eurjchem-1150	58	5	)	)	PUNCT
eurjchem-1150	58	6	(	(	PUNCT
eurjchem-1150	58	7	cocl)2	cocl)2	X
eurjchem-1150	58	8	,	,	PUNCT
eurjchem-1150	58	9	dmso	dmso	NOUN
eurjchem-1150	58	10	,	,	PUNCT
eurjchem-1150	58	11	ch2cl2	ch2cl2	PROPN
eurjchem-1150	58	12	,	,	PUNCT
eurjchem-1150	58	13	et3n	et3n	PROPN
eurjchem-1150	58	14	,	,	PUNCT
eurjchem-1150	58	15	‐78	‐78	ADJ
eurjchem-1150	58	16	°	°	NOUN
eurjchem-1150	58	17	c	c	NOUN
eurjchem-1150	58	18	.	.	PUNCT
eurjchem-1150	59	1	(	(	PUNCT
eurjchem-1150	59	2	ii	ii	NOUN
eurjchem-1150	59	3	)	)	PUNCT
eurjchem-1150	59	4	ph3pchcooet	ph3pchcooet	NOUN
eurjchem-1150	59	5	,	,	PUNCT
eurjchem-1150	59	6	meoh	meoh	NOUN
eurjchem-1150	59	7	,	,	PUNCT
eurjchem-1150	59	8	‐50	‐50	NOUN
eurjchem-1150	59	9	°	°	ADP
eurjchem-1150	59	10	c	c	NOUN
eurjchem-1150	59	11	to	to	PART
eurjchem-1150	59	12	rt	rt	PROPN
eurjchem-1150	59	13	,	,	PUNCT
eurjchem-1150	59	14	(	(	PUNCT
eurjchem-1150	59	15	88	88	NUM
eurjchem-1150	59	16	%	%	NOUN
eurjchem-1150	59	17	in	in	ADP
eurjchem-1150	59	18	two	two	NUM
eurjchem-1150	59	19	steps	step	NOUN
eurjchem-1150	59	20	)	)	PUNCT
eurjchem-1150	59	21	.	.	PUNCT
eurjchem-1150	60	1	e	e	X
eurjchem-1150	60	2	)	)	PUNCT
eurjchem-1150	60	3	dibal‐h	dibal‐h	NOUN
eurjchem-1150	60	4	,	,	PUNCT
eurjchem-1150	60	5	ch2cl2	ch2cl2	PROPN
eurjchem-1150	60	6	,	,	PUNCT
eurjchem-1150	60	7	‐78	‐78	ADJ
eurjchem-1150	60	8	°	°	NOUN
eurjchem-1150	60	9	c	c	NOUN
eurjchem-1150	60	10	,	,	PUNCT
eurjchem-1150	60	11	30	30	NUM
eurjchem-1150	60	12	min	min	NOUN
eurjchem-1150	60	13	.	.	PROPN
eurjchem-1150	61	1	f	f	X
eurjchem-1150	61	2	)	)	PUNCT
eurjchem-1150	61	3	mg	mg	PROPN
eurjchem-1150	61	4	,	,	PUNCT
eurjchem-1150	61	5	nbubr	nbubr	NOUN
eurjchem-1150	61	6	,	,	PUNCT
eurjchem-1150	61	7	thf	thf	NOUN
eurjchem-1150	61	8	,	,	PUNCT
eurjchem-1150	61	9	(	(	PUNCT
eurjchem-1150	61	10	66	66	NUM
eurjchem-1150	61	11	%	%	NOUN
eurjchem-1150	61	12	in	in	ADP
eurjchem-1150	61	13	two	two	NUM
eurjchem-1150	61	14	steps	step	NOUN
eurjchem-1150	61	15	)	)	PUNCT
eurjchem-1150	61	16	.	.	PUNCT
eurjchem-1150	62	1	g	g	NOUN
eurjchem-1150	62	2	)	)	PUNCT
eurjchem-1150	62	3	ac2o	ac2o	PROPN
eurjchem-1150	62	4	,	,	PUNCT
eurjchem-1150	62	5	dmap	dmap	NOUN
eurjchem-1150	62	6	,	,	PUNCT
eurjchem-1150	62	7	pyridine	pyridine	NOUN
eurjchem-1150	62	8	,	,	PUNCT
eurjchem-1150	62	9	ch2cl2	ch2cl2	PROPN
eurjchem-1150	62	10	,	,	PUNCT
eurjchem-1150	62	11	rt	rt	PROPN
eurjchem-1150	62	12	,	,	PUNCT
eurjchem-1150	62	13	3	3	NUM
eurjchem-1150	62	14	h	h	NOUN
eurjchem-1150	62	15	,	,	PUNCT
eurjchem-1150	62	16	99	99	NUM
eurjchem-1150	62	17	%	%	NOUN
eurjchem-1150	62	18	.	.	PUNCT
eurjchem-1150	63	1	h	h	X
eurjchem-1150	63	2	)	)	PUNCT
eurjchem-1150	63	3	tbaf	tbaf	ADJ
eurjchem-1150	63	4	,	,	PUNCT
eurjchem-1150	63	5	thf	thf	PROPN
eurjchem-1150	63	6	,	,	PUNCT
eurjchem-1150	63	7	rt	rt	PROPN
eurjchem-1150	63	8	,	,	PUNCT
eurjchem-1150	63	9	5	5	NUM
eurjchem-1150	63	10	h	h	NOUN
eurjchem-1150	63	11	,	,	PUNCT
eurjchem-1150	63	12	92	92	NUM
eurjchem-1150	63	13	%	%	NOUN
eurjchem-1150	63	14	.	.	PUNCT
eurjchem-1150	64	1	i	i	PRON
eurjchem-1150	64	2	)	)	PUNCT
eurjchem-1150	64	3	(	(	PUNCT
eurjchem-1150	64	4	i	i	NOUN
eurjchem-1150	64	5	)	)	PUNCT
eurjchem-1150	64	6	(	(	PUNCT
eurjchem-1150	64	7	cocl)2	cocl)2	X
eurjchem-1150	64	8	,	,	PUNCT
eurjchem-1150	64	9	dmso	dmso	NOUN
eurjchem-1150	64	10	,	,	PUNCT
eurjchem-1150	64	11	ch2cl2	ch2cl2	PROPN
eurjchem-1150	64	12	,	,	PUNCT
eurjchem-1150	64	13	et3n	et3n	PROPN
eurjchem-1150	64	14	,	,	PUNCT
eurjchem-1150	64	15	‐78	‐78	ADJ
eurjchem-1150	64	16	°	°	NOUN
eurjchem-1150	64	17	c	c	NOUN
eurjchem-1150	64	18	.	.	PUNCT
eurjchem-1150	65	1	(	(	PUNCT
eurjchem-1150	65	2	ii	ii	NOUN
eurjchem-1150	65	3	)	)	PUNCT
eurjchem-1150	65	4	(	(	PUNCT
eurjchem-1150	65	5	f3cch2o)2poch2cooet	f3cch2o)2poch2cooet	PROPN
eurjchem-1150	65	6	,	,	PUNCT
eurjchem-1150	65	7	18‐	18‐	NUM
eurjchem-1150	65	8	crown	crown	NOUN
eurjchem-1150	65	9	ether	ether	NOUN
eurjchem-1150	65	10	,	,	PUNCT
eurjchem-1150	65	11	khmds	khmds	NOUN
eurjchem-1150	65	12	,	,	PUNCT
eurjchem-1150	65	13	dry	dry	ADJ
eurjchem-1150	65	14	thf	thf	NOUN
eurjchem-1150	65	15	,	,	PUNCT
eurjchem-1150	65	16	‐78	‐78	ADJ
eurjchem-1150	65	17	°	°	NOUN
eurjchem-1150	65	18	c	c	NOUN
eurjchem-1150	65	19	,	,	PUNCT
eurjchem-1150	65	20	4	4	NUM
eurjchem-1150	65	21	h	h	NOUN
eurjchem-1150	65	22	,	,	PUNCT
eurjchem-1150	65	23	(	(	PUNCT
eurjchem-1150	65	24	80	80	NUM
eurjchem-1150	65	25	%	%	NOUN
eurjchem-1150	65	26	in	in	ADP
eurjchem-1150	65	27	two	two	NUM
eurjchem-1150	65	28	steps	step	NOUN
eurjchem-1150	65	29	)	)	PUNCT
eurjchem-1150	65	30	.	.	PUNCT
eurjchem-1150	66	1	j	j	X
eurjchem-1150	66	2	)	)	PUNCT
eurjchem-1150	66	3	tsoh	tsoh	PROPN
eurjchem-1150	66	4	,	,	PUNCT
eurjchem-1150	66	5	meoh	meoh	NOUN
eurjchem-1150	66	6	,	,	PUNCT
eurjchem-1150	66	7	2	2	NUM
eurjchem-1150	66	8	h	h	NOUN
eurjchem-1150	66	9	,	,	PUNCT
eurjchem-1150	66	10	93	93	NUM
eurjchem-1150	66	11	%	%	NOUN
eurjchem-1150	66	12	.	.	PUNCT
eurjchem-1150	67	1	scheme	scheme	NOUN
eurjchem-1150	67	2	1	1	NUM
eurjchem-1150	67	3	13c	13c	NOUN
eurjchem-1150	67	4	nmr	nmr	NOUN
eurjchem-1150	67	5	(	(	PUNCT
eurjchem-1150	67	6	75	75	NUM
eurjchem-1150	67	7	mhz	mhz	NOUN
eurjchem-1150	67	8	,	,	PUNCT
eurjchem-1150	67	9	cdcl3	cdcl3	PROPN
eurjchem-1150	67	10	,	,	PUNCT
eurjchem-1150	67	11	δ	δ	PROPN
eurjchem-1150	67	12	,	,	PUNCT
eurjchem-1150	67	13	ppm	ppm	NUM
eurjchem-1150	67	14	):	):	PUNCT
eurjchem-1150	67	15	13.9	13.9	NUM
eurjchem-1150	67	16	,	,	PUNCT
eurjchem-1150	67	17	26.2	26.2	NUM
eurjchem-1150	67	18	,	,	PUNCT
eurjchem-1150	67	19	61.7	61.7	NUM
eurjchem-1150	67	20	,	,	PUNCT
eurjchem-1150	67	21	76.9	76.9	NUM
eurjchem-1150	67	22	,	,	PUNCT
eurjchem-1150	67	23	113.5	113.5	NUM
eurjchem-1150	67	24	,	,	PUNCT
eurjchem-1150	67	25	169.5	169.5	NUM
eurjchem-1150	67	26	.	.	PUNCT
eurjchem-1150	68	1	esi‐ms	esi‐ms	PROPN
eurjchem-1150	68	2	(	(	PUNCT
eurjchem-1150	68	3	m	m	PROPN
eurjchem-1150	68	4	/	/	SYM
eurjchem-1150	68	5	z	z	NOUN
eurjchem-1150	68	6	):	):	PUNCT
eurjchem-1150	68	7	247	247	NUM
eurjchem-1150	68	8	(	(	PUNCT
eurjchem-1150	68	9	m+1)+	m+1)+	NOUN
eurjchem-1150	68	10	,	,	PUNCT
eurjchem-1150	68	11	269	269	NUM
eurjchem-1150	68	12	(	(	PUNCT
eurjchem-1150	68	13	m+na)+	m+na)+	PROPN
eurjchem-1150	68	14	.	.	NOUN
eurjchem-1150	68	15	2.2.2	2.2.2	NUM
eurjchem-1150	68	16	.	.	PUNCT
eurjchem-1150	68	17	synthesis	synthesis	NOUN
eurjchem-1150	68	18	of	of	ADP
eurjchem-1150	68	19	(	(	PUNCT
eurjchem-1150	68	20	(	(	PUNCT
eurjchem-1150	68	21	4s,5s)‐2,2‐dimethyl‐1,3‐dioxolane‐4,5‐	4s,5s)‐2,2‐dimethyl‐1,3‐dioxolane‐4,5‐	NUM
eurjchem-1150	68	22	diyl)dimethanol	diyl)dimethanol	PROPN
eurjchem-1150	68	23	(	(	PUNCT
eurjchem-1150	68	24	8)	8)	NUM
eurjchem-1150	68	25	a	a	DET
eurjchem-1150	68	26	solution	solution	NOUN
eurjchem-1150	68	27	of	of	ADP
eurjchem-1150	68	28	compound	compound	NOUN
eurjchem-1150	68	29	7	7	NUM
eurjchem-1150	68	30	(	(	PUNCT
eurjchem-1150	68	31	6	6	NUM
eurjchem-1150	68	32	g	g	NOUN
eurjchem-1150	68	33	,	,	PUNCT
eurjchem-1150	68	34	24.4	24.4	NUM
eurjchem-1150	68	35	mmol	mmol	NOUN
eurjchem-1150	68	36	)	)	PUNCT
eurjchem-1150	68	37	in	in	ADP
eurjchem-1150	68	38	thf	thf	NOUN
eurjchem-1150	68	39	(	(	PUNCT
eurjchem-1150	68	40	20	20	NUM
eurjchem-1150	68	41	ml	ml	NOUN
eurjchem-1150	68	42	)	)	PUNCT
eurjchem-1150	68	43	was	be	AUX
eurjchem-1150	68	44	slowly	slowly	ADV
eurjchem-1150	68	45	added	add	VERB
eurjchem-1150	68	46	to	to	ADP
eurjchem-1150	68	47	a	a	DET
eurjchem-1150	68	48	suspension	suspension	NOUN
eurjchem-1150	68	49	of	of	ADP
eurjchem-1150	68	50	lialh4	lialh4	NOUN
eurjchem-1150	68	51	(	(	PUNCT
eurjchem-1150	68	52	3.7	3.7	NUM
eurjchem-1150	68	53	g	g	NOUN
eurjchem-1150	68	54	,	,	PUNCT
eurjchem-1150	68	55	97.5	97.5	NUM
eurjchem-1150	68	56	mmol	mmol	NOUN
eurjchem-1150	68	57	)	)	PUNCT
eurjchem-1150	68	58	in	in	ADP
eurjchem-1150	68	59	thf	thf	NOUN
eurjchem-1150	68	60	(	(	PUNCT
eurjchem-1150	68	61	100	100	NUM
eurjchem-1150	68	62	ml	ml	NOUN
eurjchem-1150	68	63	)	)	PUNCT
eurjchem-1150	68	64	at	at	ADP
eurjchem-1150	68	65	0	0	NUM
eurjchem-1150	68	66	°	°	ADP
eurjchem-1150	68	67	c	c	NOUN
eurjchem-1150	68	68	over	over	ADP
eurjchem-1150	68	69	a	a	DET
eurjchem-1150	68	70	period	period	NOUN
eurjchem-1150	68	71	of	of	ADP
eurjchem-1150	68	72	20	20	NUM
eurjchem-1150	68	73	min	min	NOUN
eurjchem-1150	68	74	under	under	ADP
eurjchem-1150	68	75	nitrogen	nitrogen	NOUN
eurjchem-1150	68	76	atmosphere	atmosphere	NOUN
eurjchem-1150	68	77	.	.	PUNCT
eurjchem-1150	69	1	after	after	ADP
eurjchem-1150	69	2	2	2	NUM
eurjchem-1150	69	3	h	h	NOUN
eurjchem-1150	69	4	,	,	PUNCT
eurjchem-1150	69	5	aqueous	aqueous	ADJ
eurjchem-1150	69	6	nh4cl	nh4cl	PROPN
eurjchem-1150	69	7	(	(	PUNCT
eurjchem-1150	69	8	10	10	NUM
eurjchem-1150	69	9	%	%	NOUN
eurjchem-1150	69	10	,	,	PUNCT
eurjchem-1150	69	11	w	w	NOUN
eurjchem-1150	69	12	:	:	SYM
eurjchem-1150	69	13	v	v	NOUN
eurjchem-1150	69	14	,	,	PUNCT
eurjchem-1150	69	15	20	20	NUM
eurjchem-1150	69	16	ml	ml	NOUN
eurjchem-1150	69	17	)	)	PUNCT
eurjchem-1150	69	18	was	be	AUX
eurjchem-1150	69	19	added	add	VERB
eurjchem-1150	69	20	and	and	CCONJ
eurjchem-1150	69	21	the	the	DET
eurjchem-1150	69	22	reaction	reaction	NOUN
eurjchem-1150	69	23	mixture	mixture	NOUN
eurjchem-1150	69	24	was	be	AUX
eurjchem-1150	69	25	filtered	filter	VERB
eurjchem-1150	69	26	through	through	ADP
eurjchem-1150	69	27	celite	celite	ADJ
eurjchem-1150	69	28	.	.	PUNCT
eurjchem-1150	70	1	the	the	DET
eurjchem-1150	70	2	filtrate	filtrate	NOUN
eurjchem-1150	70	3	was	be	AUX
eurjchem-1150	70	4	dried	dry	VERB
eurjchem-1150	70	5	over	over	ADP
eurjchem-1150	70	6	anhydrous	anhydrous	ADJ
eurjchem-1150	70	7	mgso4	mgso4	NOUN
eurjchem-1150	70	8	and	and	CCONJ
eurjchem-1150	70	9	evaporated	evaporate	VERB
eurjchem-1150	70	10	under	under	ADP
eurjchem-1150	70	11	vacuum	vacuum	NOUN
eurjchem-1150	70	12	.	.	PUNCT
eurjchem-1150	71	1	the	the	DET
eurjchem-1150	71	2	crude	crude	ADJ
eurjchem-1150	71	3	product	product	NOUN
eurjchem-1150	71	4	was	be	AUX
eurjchem-1150	71	5	purified	purify	VERB
eurjchem-1150	71	6	by	by	ADP
eurjchem-1150	71	7	flash	flash	NOUN
eurjchem-1150	71	8	column	column	NOUN
eurjchem-1150	71	9	chromatography	chromatography	NOUN
eurjchem-1150	71	10	using	use	VERB
eurjchem-1150	71	11	etoac	etoac	ADJ
eurjchem-1150	71	12	as	as	ADP
eurjchem-1150	71	13	eluent	eluent	NOUN
eurjchem-1150	71	14	to	to	PART
eurjchem-1150	71	15	afford	afford	VERB
eurjchem-1150	71	16	pure	pure	ADJ
eurjchem-1150	71	17	compound	compound	NOUN
eurjchem-1150	71	18	8	8	NUM
eurjchem-1150	71	19	(	(	PUNCT
eurjchem-1150	71	20	scheme	scheme	NOUN
eurjchem-1150	71	21	1	1	NUM
eurjchem-1150	71	22	)	)	PUNCT
eurjchem-1150	71	23	.	.	PUNCT
eurjchem-1150	72	1	color	color	NOUN
eurjchem-1150	72	2	:	:	PUNCT
eurjchem-1150	72	3	colorless	colorless	ADJ
eurjchem-1150	72	4	liquid	liquid	NOUN
eurjchem-1150	72	5	.	.	PUNCT
eurjchem-1150	73	1	yield	yield	NOUN
eurjchem-1150	73	2	:	:	PUNCT
eurjchem-1150	73	3	3.35	3.35	NUM
eurjchem-1150	73	4	g	g	NOUN
eurjchem-1150	73	5	,	,	PUNCT
eurjchem-1150	73	6	85	85	NUM
eurjchem-1150	73	7	%	%	NOUN
eurjchem-1150	73	8	.	.	PUNCT
eurjchem-1150	74	1	ft‐ir	ft‐ir	NOUN
eurjchem-1150	74	2	(	(	PUNCT
eurjchem-1150	74	3	neat	neat	ADJ
eurjchem-1150	74	4	,	,	PUNCT
eurjchem-1150	74	5	ν	ν	NOUN
eurjchem-1150	74	6	,	,	PUNCT
eurjchem-1150	74	7	cm‐1	cm‐1	PROPN
eurjchem-1150	74	8	):	):	PUNCT
eurjchem-1150	74	9	3403	3403	NUM
eurjchem-1150	74	10	.	.	PUNCT
eurjchem-1150	75	1	1h	1h	NUM
eurjchem-1150	75	2	nmr	nmr	NOUN
eurjchem-1150	75	3	(	(	PUNCT
eurjchem-1150	75	4	300	300	NUM
eurjchem-1150	75	5	mhz	mhz	NOUN
eurjchem-1150	75	6	,	,	PUNCT
eurjchem-1150	75	7	cdcl3	cdcl3	PROPN
eurjchem-1150	75	8	,	,	PUNCT
eurjchem-1150	75	9	δ	δ	PROPN
eurjchem-1150	75	10	,	,	PUNCT
eurjchem-1150	75	11	ppm	ppm	NUM
eurjchem-1150	75	12	):	):	PUNCT
eurjchem-1150	75	13	1.43	1.43	NUM
eurjchem-1150	75	14	(	(	PUNCT
eurjchem-1150	75	15	s	s	PROPN
eurjchem-1150	75	16	,	,	PUNCT
eurjchem-1150	75	17	6h	6h	NUM
eurjchem-1150	75	18	,	,	PUNCT
eurjchem-1150	75	19	(	(	PUNCT
eurjchem-1150	75	20	ch3)2c	ch3)2c	PROPN
eurjchem-1150	75	21	)	)	PUNCT
eurjchem-1150	75	22	,	,	PUNCT
eurjchem-1150	75	23	2.77	2.77	NUM
eurjchem-1150	75	24	(	(	PUNCT
eurjchem-1150	75	25	br	br	NOUN
eurjchem-1150	75	26	.	.	PUNCT
eurjchem-1150	75	27	s	s	PART
eurjchem-1150	75	28	,	,	PUNCT
eurjchem-1150	75	29	2h	2h	NUM
eurjchem-1150	75	30	,	,	PUNCT
eurjchem-1150	75	31	2	2	NUM
eurjchem-1150	75	32	‐oh	‐oh	NOUN
eurjchem-1150	75	33	)	)	PUNCT
eurjchem-1150	75	34	,	,	PUNCT
eurjchem-1150	75	35	3.68‐3.81	3.68‐3.81	NUM
eurjchem-1150	75	36	(	(	PUNCT
eurjchem-1150	75	37	m	m	PROPN
eurjchem-1150	75	38	,	,	PUNCT
eurjchem-1150	75	39	4h	4h	NOUN
eurjchem-1150	75	40	,	,	PUNCT
eurjchem-1150	75	41	ch2‐oh	ch2‐oh	NOUN
eurjchem-1150	75	42	)	)	PUNCT
eurjchem-1150	75	43	,	,	PUNCT
eurjchem-1150	75	44	3.98‐3.99	3.98‐3.99	NUM
eurjchem-1150	75	45	(	(	PUNCT
eurjchem-1150	75	46	m	m	PROPN
eurjchem-1150	75	47	,	,	PUNCT
eurjchem-1150	75	48	2h	2h	NUM
eurjchem-1150	75	49	,	,	PUNCT
eurjchem-1150	75	50	ch‐ch2‐oh	ch‐ch2‐oh	NOUN
eurjchem-1150	75	51	)	)	PUNCT
eurjchem-1150	75	52	.	.	PUNCT
eurjchem-1150	76	1	13c	13c	NOUN
eurjchem-1150	76	2	nmr	nmr	NOUN
eurjchem-1150	76	3	(	(	PUNCT
eurjchem-1150	76	4	75	75	NUM
eurjchem-1150	76	5	mhz	mhz	NOUN
eurjchem-1150	76	6	,	,	PUNCT
eurjchem-1150	76	7	cdcl3	cdcl3	PROPN
eurjchem-1150	76	8	,	,	PUNCT
eurjchem-1150	76	9	δ	δ	PROPN
eurjchem-1150	76	10	,	,	PUNCT
eurjchem-1150	76	11	ppm	ppm	NUM
eurjchem-1150	76	12	):	):	PUNCT
eurjchem-1150	76	13	δ	δ	PROPN
eurjchem-1150	76	14	26.9	26.9	NUM
eurjchem-1150	76	15	,	,	PUNCT
eurjchem-1150	76	16	62.0	62.0	NUM
eurjchem-1150	76	17	,	,	PUNCT
eurjchem-1150	76	18	78.1	78.1	NUM
eurjchem-1150	76	19	,	,	PUNCT
eurjchem-1150	76	20	109.2	109.2	NUM
eurjchem-1150	76	21	.	.	PUNCT
eurjchem-1150	77	1	esi‐ms	esi‐ms	PROPN
eurjchem-1150	77	2	(	(	PUNCT
eurjchem-1150	77	3	m	m	PROPN
eurjchem-1150	77	4	/	/	SYM
eurjchem-1150	77	5	z	z	NOUN
eurjchem-1150	77	6	):	):	PUNCT
eurjchem-1150	77	7	162	162	NUM
eurjchem-1150	77	8	(	(	PUNCT
eurjchem-1150	77	9	m+	m+	NUM
eurjchem-1150	77	10	)	)	PUNCT
eurjchem-1150	77	11	.	.	PUNCT
eurjchem-1150	78	1	[	[	X
eurjchem-1150	78	2	α]d25	α]d25	NUM
eurjchem-1150	78	3	:	:	PUNCT
eurjchem-1150	78	4	‐8.16	‐8.16	NUM
eurjchem-1150	78	5	(	(	PUNCT
eurjchem-1150	78	6	c	c	NOUN
eurjchem-1150	78	7	1	1	NUM
eurjchem-1150	78	8	,	,	PUNCT
eurjchem-1150	78	9	chcl3	chcl3	PROPN
eurjchem-1150	78	10	)	)	PUNCT
eurjchem-1150	78	11	.	.	PUNCT
eurjchem-1150	79	1	2.2.3	2.2.3	X
eurjchem-1150	79	2	.	.	X
eurjchem-1150	79	3	synthesis	synthesis	NOUN
eurjchem-1150	79	4	of	of	ADP
eurjchem-1150	79	5	(	(	PUNCT
eurjchem-1150	79	6	(	(	PUNCT
eurjchem-1150	79	7	4s,5s)‐5‐((tert‐butyldiphenylsilyloxy	4s,5s)‐5‐((tert‐butyldiphenylsilyloxy	NOUN
eurjchem-1150	79	8	)	)	PUNCT
eurjchem-1150	79	9	methyl)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl	methyl)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl	PROPN
eurjchem-1150	79	10	)	)	PUNCT
eurjchem-1150	79	11	methanol	methanol	NOUN
eurjchem-1150	79	12	(	(	PUNCT
eurjchem-1150	79	13	9	9	NUM
eurjchem-1150	79	14	)	)	PUNCT
eurjchem-1150	79	15	to	to	ADP
eurjchem-1150	79	16	a	a	DET
eurjchem-1150	79	17	stirred	stir	VERB
eurjchem-1150	79	18	solution	solution	NOUN
eurjchem-1150	79	19	of	of	ADP
eurjchem-1150	79	20	diol	diol	NOUN
eurjchem-1150	79	21	(	(	PUNCT
eurjchem-1150	79	22	8)	8)	NUM
eurjchem-1150	79	23	(	(	PUNCT
eurjchem-1150	79	24	1.62	1.62	NUM
eurjchem-1150	79	25	g	g	NOUN
eurjchem-1150	79	26	,	,	PUNCT
eurjchem-1150	79	27	10	10	NUM
eurjchem-1150	79	28	mmol	mmol	NOUN
eurjchem-1150	79	29	)	)	PUNCT
eurjchem-1150	79	30	in	in	ADP
eurjchem-1150	79	31	anhydrous	anhydrous	ADJ
eurjchem-1150	79	32	thf	thf	NOUN
eurjchem-1150	79	33	(	(	PUNCT
eurjchem-1150	79	34	50	50	NUM
eurjchem-1150	79	35	ml	ml	NOUN
eurjchem-1150	79	36	)	)	PUNCT
eurjchem-1150	79	37	,	,	PUNCT
eurjchem-1150	79	38	nah	nah	INTJ
eurjchem-1150	79	39	(	(	PUNCT
eurjchem-1150	79	40	264	264	NUM
eurjchem-1150	79	41	mg	mg	NOUN
eurjchem-1150	79	42	,	,	PUNCT
eurjchem-1150	79	43	11	11	NUM
eurjchem-1150	79	44	mmol	mmol	NOUN
eurjchem-1150	79	45	)	)	PUNCT
eurjchem-1150	79	46	was	be	AUX
eurjchem-1150	79	47	added	add	VERB
eurjchem-1150	79	48	at	at	ADP
eurjchem-1150	79	49	0	0	NUM
eurjchem-1150	79	50	°	°	ADP
eurjchem-1150	79	51	c	c	NOUN
eurjchem-1150	79	52	under	under	ADP
eurjchem-1150	79	53	nitrogen	nitrogen	NOUN
eurjchem-1150	79	54	atmosphere	atmosphere	NOUN
eurjchem-1150	79	55	and	and	CCONJ
eurjchem-1150	79	56	the	the	DET
eurjchem-1150	79	57	contents	content	NOUN
eurjchem-1150	79	58	were	be	AUX
eurjchem-1150	79	59	stirred	stir	VERB
eurjchem-1150	79	60	for	for	ADP
eurjchem-1150	79	61	30	30	NUM
eurjchem-1150	79	62	min	min	NOUN
eurjchem-1150	79	63	.	.	PUNCT
eurjchem-1150	80	1	a	a	DET
eurjchem-1150	80	2	solution	solution	NOUN
eurjchem-1150	80	3	of	of	ADP
eurjchem-1150	80	4	tert‐butylchlorodiphenylsilane	tert‐butylchlorodiphenylsilane	PROPN
eurjchem-1150	80	5	(	(	PUNCT
eurjchem-1150	80	6	tbdps‐cl	tbdps‐cl	PROPN
eurjchem-1150	80	7	)	)	PUNCT
eurjchem-1150	80	8	(	(	PUNCT
eurjchem-1150	80	9	2.74	2.74	NUM
eurjchem-1150	80	10	g	g	NOUN
eurjchem-1150	80	11	,	,	PUNCT
eurjchem-1150	80	12	10	10	NUM
eurjchem-1150	80	13	mmol	mmol	NOUN
eurjchem-1150	80	14	)	)	PUNCT
eurjchem-1150	80	15	dissolved	dissolve	VERB
eurjchem-1150	80	16	in	in	ADP
eurjchem-1150	80	17	anhydrous	anhydrous	ADJ
eurjchem-1150	80	18	thf	thf	NOUN
eurjchem-1150	80	19	(	(	PUNCT
eurjchem-1150	80	20	20	20	NUM
eurjchem-1150	80	21	ml	ml	NOUN
eurjchem-1150	80	22	)	)	PUNCT
eurjchem-1150	80	23	was	be	AUX
eurjchem-1150	80	24	added	add	VERB
eurjchem-1150	80	25	and	and	CCONJ
eurjchem-1150	80	26	stirring	stirring	NOUN
eurjchem-1150	80	27	was	be	AUX
eurjchem-1150	80	28	continued	continue	VERB
eurjchem-1150	80	29	for	for	ADP
eurjchem-1150	80	30	2	2	NUM
eurjchem-1150	80	31	h	h	NOUN
eurjchem-1150	80	32	at	at	ADP
eurjchem-1150	80	33	room	room	NOUN
eurjchem-1150	80	34	temperature	temperature	NOUN
eurjchem-1150	80	35	.	.	PUNCT
eurjchem-1150	81	1	the	the	DET
eurjchem-1150	81	2	reaction	reaction	NOUN
eurjchem-1150	81	3	mixture	mixture	NOUN
eurjchem-1150	81	4	was	be	AUX
eurjchem-1150	81	5	quenched	quench	VERB
eurjchem-1150	81	6	with	with	ADP
eurjchem-1150	81	7	water	water	NOUN
eurjchem-1150	81	8	(	(	PUNCT
eurjchem-1150	81	9	40	40	NUM
eurjchem-1150	81	10	ml	ml	NOUN
eurjchem-1150	81	11	)	)	PUNCT
eurjchem-1150	81	12	and	and	CCONJ
eurjchem-1150	81	13	thf	thf	NOUN
eurjchem-1150	81	14	was	be	AUX
eurjchem-1150	81	15	evaporated	evaporate	VERB
eurjchem-1150	81	16	.	.	PUNCT
eurjchem-1150	82	1	the	the	DET
eurjchem-1150	82	2	residue	residue	NOUN
eurjchem-1150	82	3	was	be	AUX
eurjchem-1150	82	4	extracted	extract	VERB
eurjchem-1150	82	5	with	with	ADP
eurjchem-1150	82	6	ch2cl2	ch2cl2	X
eurjchem-1150	82	7	(	(	PUNCT
eurjchem-1150	82	8	3×10	3×10	NUM
eurjchem-1150	82	9	ml	ml	NOUN
eurjchem-1150	82	10	)	)	PUNCT
eurjchem-1150	82	11	,	,	PUNCT
eurjchem-1150	82	12	dried	dry	VERB
eurjchem-1150	82	13	over	over	ADP
eurjchem-1150	82	14	anhydrous	anhydrous	ADJ
eurjchem-1150	82	15	mgso4	mgso4	NOUN
eurjchem-1150	82	16	,	,	PUNCT
eurjchem-1150	82	17	and	and	CCONJ
eurjchem-1150	82	18	concentrated	concentrate	VERB
eurjchem-1150	82	19	under	under	ADP
eurjchem-1150	82	20	vacuum	vacuum	NOUN
eurjchem-1150	82	21	.	.	PUNCT
eurjchem-1150	83	1	the	the	DET
eurjchem-1150	83	2	crude	crude	ADJ
eurjchem-1150	83	3	product	product	NOUN
eurjchem-1150	83	4	was	be	AUX
eurjchem-1150	83	5	subjected	subject	VERB
eurjchem-1150	83	6	to	to	PART
eurjchem-1150	83	7	flash	flash	VERB
eurjchem-1150	83	8	column	column	NOUN
eurjchem-1150	83	9	chromatography	chromatography	NOUN
eurjchem-1150	83	10	(	(	PUNCT
eurjchem-1150	83	11	hexane	hexane	NOUN
eurjchem-1150	83	12	:	:	PUNCT
eurjchem-1150	83	13	etoac	etoac	ADJ
eurjchem-1150	83	14	,	,	PUNCT
eurjchem-1150	83	15	4:1	4:1	NUM
eurjchem-1150	83	16	,	,	PUNCT
eurjchem-1150	83	17	v	v	NOUN
eurjchem-1150	83	18	:	:	SYM
eurjchem-1150	83	19	v	v	NOUN
eurjchem-1150	83	20	)	)	PUNCT
eurjchem-1150	83	21	to	to	PART
eurjchem-1150	83	22	afford	afford	VERB
eurjchem-1150	83	23	compound	compound	VERB
eurjchem-1150	83	24	9	9	NUM
eurjchem-1150	83	25	(	(	PUNCT
eurjchem-1150	83	26	scheme	scheme	NOUN
eurjchem-1150	83	27	1	1	NUM
eurjchem-1150	83	28	)	)	PUNCT
eurjchem-1150	83	29	.	.	PUNCT
eurjchem-1150	84	1	color	color	NOUN
eurjchem-1150	84	2	:	:	PUNCT
eurjchem-1150	84	3	colorless	colorless	ADJ
eurjchem-1150	84	4	oil	oil	NOUN
eurjchem-1150	84	5	.	.	PUNCT
eurjchem-1150	85	1	yield	yield	NOUN
eurjchem-1150	85	2	:	:	PUNCT
eurjchem-1150	85	3	3.6	3.6	NUM
eurjchem-1150	85	4	perla	perla	NOUN
eurjchem-1150	85	5	and	and	CCONJ
eurjchem-1150	85	6	fadnavis	fadnavis	NOUN
eurjchem-1150	85	7	/	/	SYM
eurjchem-1150	85	8	european	european	PROPN
eurjchem-1150	85	9	journal	journal	PROPN
eurjchem-1150	85	10	of	of	ADP
eurjchem-1150	85	11	chemistry	chemistry	NOUN
eurjchem-1150	85	12	6	6	NUM
eurjchem-1150	85	13	(	(	PUNCT
eurjchem-1150	85	14	1	1	NUM
eurjchem-1150	85	15	)	)	PUNCT
eurjchem-1150	85	16	(	(	PUNCT
eurjchem-1150	85	17	2015	2015	NUM
eurjchem-1150	85	18	)	)	PUNCT
eurjchem-1150	85	19	93‐97	93‐97	NUM
eurjchem-1150	86	1	95	95	NUM
eurjchem-1150	86	2	g	g	NOUN
eurjchem-1150	86	3	,	,	PUNCT
eurjchem-1150	86	4	90	90	NUM
eurjchem-1150	86	5	%	%	NOUN
eurjchem-1150	86	6	.	.	PUNCT
eurjchem-1150	87	1	ft‐ir	ft‐ir	NOUN
eurjchem-1150	87	2	(	(	PUNCT
eurjchem-1150	87	3	neat	neat	ADJ
eurjchem-1150	87	4	,	,	PUNCT
eurjchem-1150	87	5	ν	ν	NOUN
eurjchem-1150	87	6	,	,	PUNCT
eurjchem-1150	87	7	cm‐1	cm‐1	PROPN
eurjchem-1150	87	8	):	):	PUNCT
eurjchem-1150	87	9	3466	3466	NUM
eurjchem-1150	87	10	,	,	PUNCT
eurjchem-1150	87	11	2931	2931	NUM
eurjchem-1150	87	12	,	,	PUNCT
eurjchem-1150	87	13	1428	1428	NUM
eurjchem-1150	87	14	,	,	PUNCT
eurjchem-1150	87	15	1245	1245	NUM
eurjchem-1150	87	16	,	,	PUNCT
eurjchem-1150	87	17	1080	1080	NUM
eurjchem-1150	87	18	,	,	PUNCT
eurjchem-1150	87	19	702	702	NUM
eurjchem-1150	87	20	.	.	NOUN
eurjchem-1150	87	21	1h	1h	NUM
eurjchem-1150	87	22	nmr	nmr	NOUN
eurjchem-1150	87	23	(	(	PUNCT
eurjchem-1150	87	24	300	300	NUM
eurjchem-1150	87	25	mhz	mhz	NOUN
eurjchem-1150	87	26	,	,	PUNCT
eurjchem-1150	87	27	cdcl3	cdcl3	PROPN
eurjchem-1150	87	28	,	,	PUNCT
eurjchem-1150	87	29	δ	δ	PROPN
eurjchem-1150	87	30	,	,	PUNCT
eurjchem-1150	87	31	ppm	ppm	NOUN
eurjchem-1150	87	32	):	):	PUNCT
eurjchem-1150	87	33	1.06	1.06	NUM
eurjchem-1150	87	34	(	(	PUNCT
eurjchem-1150	87	35	s	s	PROPN
eurjchem-1150	87	36	,	,	PUNCT
eurjchem-1150	87	37	9h	9h	NUM
eurjchem-1150	87	38	,	,	PUNCT
eurjchem-1150	87	39	(	(	PUNCT
eurjchem-1150	87	40	ch3)3c‐	ch3)3c‐	PROPN
eurjchem-1150	87	41	si	si	PROPN
eurjchem-1150	87	42	)	)	PUNCT
eurjchem-1150	87	43	,	,	PUNCT
eurjchem-1150	87	44	1.38	1.38	NUM
eurjchem-1150	87	45	(	(	PUNCT
eurjchem-1150	87	46	s	s	PROPN
eurjchem-1150	87	47	,	,	PUNCT
eurjchem-1150	87	48	3h	3h	NUM
eurjchem-1150	87	49	,	,	PUNCT
eurjchem-1150	87	50	ch3‐c‐o	ch3‐c‐o	PROPN
eurjchem-1150	87	51	)	)	PUNCT
eurjchem-1150	87	52	,	,	PUNCT
eurjchem-1150	87	53	1.41	1.41	NUM
eurjchem-1150	87	54	(	(	PUNCT
eurjchem-1150	87	55	s	s	PROPN
eurjchem-1150	87	56	,	,	PUNCT
eurjchem-1150	87	57	3h	3h	NUM
eurjchem-1150	87	58	,	,	PUNCT
eurjchem-1150	87	59	ch3‐c‐o	ch3‐c‐o	PROPN
eurjchem-1150	87	60	)	)	PUNCT
eurjchem-1150	87	61	,	,	PUNCT
eurjchem-1150	87	62	3.63‐3.84	3.63‐3.84	NUM
eurjchem-1150	87	63	(	(	PUNCT
eurjchem-1150	87	64	m	m	PROPN
eurjchem-1150	87	65	,	,	PUNCT
eurjchem-1150	87	66	4h	4h	PROPN
eurjchem-1150	87	67	,	,	PUNCT
eurjchem-1150	87	68	ch2‐oh	ch2‐oh	PROPN
eurjchem-1150	87	69	,	,	PUNCT
eurjchem-1150	87	70	ch2‐osi	ch2‐osi	PROPN
eurjchem-1150	87	71	)	)	PUNCT
eurjchem-1150	87	72	,	,	PUNCT
eurjchem-1150	87	73	3.93‐3.99	3.93‐3.99	NUM
eurjchem-1150	87	74	(	(	PUNCT
eurjchem-1150	87	75	m	m	PROPN
eurjchem-1150	87	76	,	,	PUNCT
eurjchem-1150	87	77	1h	1h	NUM
eurjchem-1150	87	78	,	,	PUNCT
eurjchem-1150	87	79	ch‐ch2‐oh	ch‐ch2‐oh	NOUN
eurjchem-1150	87	80	)	)	PUNCT
eurjchem-1150	87	81	,	,	PUNCT
eurjchem-1150	87	82	4.04‐	4.04‐	NUM
eurjchem-1150	87	83	4.10	4.10	NUM
eurjchem-1150	87	84	(	(	PUNCT
eurjchem-1150	87	85	m	m	PROPN
eurjchem-1150	87	86	,	,	PUNCT
eurjchem-1150	87	87	1h	1h	NUM
eurjchem-1150	87	88	,	,	PUNCT
eurjchem-1150	87	89	ch‐ch2‐osi	ch‐ch2‐osi	NOUN
eurjchem-1150	87	90	)	)	PUNCT
eurjchem-1150	87	91	,	,	PUNCT
eurjchem-1150	87	92	7.36‐7.43	7.36‐7.43	NUM
eurjchem-1150	87	93	(	(	PUNCT
eurjchem-1150	87	94	m	m	PROPN
eurjchem-1150	87	95	,	,	PUNCT
eurjchem-1150	87	96	6h	6h	NUM
eurjchem-1150	87	97	,	,	PUNCT
eurjchem-1150	87	98	ar‐h	ar‐h	PROPN
eurjchem-1150	87	99	)	)	PUNCT
eurjchem-1150	87	100	,	,	PUNCT
eurjchem-1150	87	101	7.64‐7.68	7.64‐7.68	NUM
eurjchem-1150	87	102	(	(	PUNCT
eurjchem-1150	87	103	m	m	PROPN
eurjchem-1150	87	104	,	,	PUNCT
eurjchem-1150	87	105	4h	4h	NOUN
eurjchem-1150	87	106	,	,	PUNCT
eurjchem-1150	87	107	ar‐h	ar‐h	PROPN
eurjchem-1150	87	108	)	)	PUNCT
eurjchem-1150	87	109	.	.	PUNCT
eurjchem-1150	88	1	13c	13c	NOUN
eurjchem-1150	88	2	nmr	nmr	NOUN
eurjchem-1150	88	3	(	(	PUNCT
eurjchem-1150	88	4	75	75	NUM
eurjchem-1150	88	5	mhz	mhz	NOUN
eurjchem-1150	88	6	,	,	PUNCT
eurjchem-1150	88	7	cdcl3	cdcl3	PROPN
eurjchem-1150	88	8	,	,	PUNCT
eurjchem-1150	88	9	δ	δ	PROPN
eurjchem-1150	88	10	,	,	PUNCT
eurjchem-1150	88	11	ppm	ppm	NUM
eurjchem-1150	88	12	):	):	PUNCT
eurjchem-1150	88	13	19.1	19.1	NUM
eurjchem-1150	88	14	,	,	PUNCT
eurjchem-1150	88	15	26.7	26.7	NUM
eurjchem-1150	88	16	,	,	PUNCT
eurjchem-1150	88	17	26.9	26.9	NUM
eurjchem-1150	88	18	,	,	PUNCT
eurjchem-1150	88	19	27.0	27.0	NUM
eurjchem-1150	88	20	,	,	PUNCT
eurjchem-1150	88	21	62.5	62.5	NUM
eurjchem-1150	88	22	,	,	PUNCT
eurjchem-1150	88	23	64.1	64.1	NUM
eurjchem-1150	88	24	,	,	PUNCT
eurjchem-1150	88	25	77.4	77.4	NUM
eurjchem-1150	88	26	,	,	PUNCT
eurjchem-1150	88	27	79.5	79.5	NUM
eurjchem-1150	88	28	,	,	PUNCT
eurjchem-1150	88	29	109.1	109.1	NUM
eurjchem-1150	88	30	,	,	PUNCT
eurjchem-1150	88	31	127.7	127.7	NUM
eurjchem-1150	88	32	,	,	PUNCT
eurjchem-1150	88	33	127.8	127.8	NUM
eurjchem-1150	88	34	,	,	PUNCT
eurjchem-1150	88	35	129.8	129.8	NUM
eurjchem-1150	88	36	,	,	PUNCT
eurjchem-1150	88	37	129.9	129.9	NUM
eurjchem-1150	88	38	,	,	PUNCT
eurjchem-1150	88	39	132.8	132.8	NUM
eurjchem-1150	88	40	,	,	PUNCT
eurjchem-1150	88	41	135.5	135.5	NUM
eurjchem-1150	88	42	.	.	PUNCT
eurjchem-1150	89	1	esi‐ms	esi‐ms	PROPN
eurjchem-1150	89	2	(	(	PUNCT
eurjchem-1150	89	3	m	m	PROPN
eurjchem-1150	89	4	/	/	SYM
eurjchem-1150	89	5	z	z	NOUN
eurjchem-1150	89	6	):	):	PUNCT
eurjchem-1150	89	7	423	423	NUM
eurjchem-1150	89	8	(	(	PUNCT
eurjchem-1150	89	9	m+na)+	m+na)+	NOUN
eurjchem-1150	89	10	.	.	PUNCT
eurjchem-1150	90	1	[	[	X
eurjchem-1150	90	2	α]d25	α]d25	NOUN
eurjchem-1150	90	3	:	:	PUNCT
eurjchem-1150	90	4	‐1.5	‐1.5	NOUN
eurjchem-1150	90	5	(	(	PUNCT
eurjchem-1150	90	6	c	c	PROPN
eurjchem-1150	90	7	14.5	14.5	NUM
eurjchem-1150	90	8	,	,	PUNCT
eurjchem-1150	90	9	chcl3	chcl3	PROPN
eurjchem-1150	90	10	)	)	PUNCT
eurjchem-1150	90	11	.	.	PUNCT
eurjchem-1150	91	1	2.2.4	2.2.4	NUM
eurjchem-1150	91	2	.	.	X
eurjchem-1150	91	3	synthesis	synthesis	NOUN
eurjchem-1150	91	4	of	of	ADP
eurjchem-1150	91	5	(	(	PUNCT
eurjchem-1150	91	6	z)‐ethyl	z)‐ethyl	PROPN
eurjchem-1150	91	7	3‐((4s,5s)‐5‐((tert‐butyl	3‐((4s,5s)‐5‐((tert‐butyl	PROPN
eurjchem-1150	91	8	diphenylsilyloxy)methyl)‐2,2‐dimethyl‐1,3‐dioxolan	diphenylsilyloxy)methyl)‐2,2‐dimethyl‐1,3‐dioxolan	PROPN
eurjchem-1150	91	9	‐4‐yl	‐4‐yl	NOUN
eurjchem-1150	91	10	)	)	PUNCT
eurjchem-1150	91	11	acrylate	acrylate	NOUN
eurjchem-1150	91	12	(	(	PUNCT
eurjchem-1150	91	13	10a	10a	NUM
eurjchem-1150	91	14	)	)	PUNCT
eurjchem-1150	91	15	and	and	CCONJ
eurjchem-1150	91	16	(	(	PUNCT
eurjchem-1150	91	17	e)‐ethyl	e)‐ethyl	PROPN
eurjchem-1150	91	18	3‐((4s,5s)‐5‐((tert‐butyl	3‐((4s,5s)‐5‐((tert‐butyl	PROPN
eurjchem-1150	91	19	diphenylsilyloxy	diphenylsilyloxy	PROPN
eurjchem-1150	91	20	)	)	PUNCT
eurjchem-1150	91	21	methyl)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl	methyl)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl	PROPN
eurjchem-1150	91	22	)	)	PUNCT
eurjchem-1150	91	23	acrylate	acrylate	NOUN
eurjchem-1150	91	24	(	(	PUNCT
eurjchem-1150	91	25	10b	10b	NOUN
eurjchem-1150	91	26	)	)	PUNCT
eurjchem-1150	91	27	to	to	ADP
eurjchem-1150	91	28	a	a	DET
eurjchem-1150	91	29	solution	solution	NOUN
eurjchem-1150	91	30	of	of	ADP
eurjchem-1150	91	31	oxalyl	oxalyl	ADJ
eurjchem-1150	91	32	chloride	chloride	NOUN
eurjchem-1150	91	33	(	(	PUNCT
eurjchem-1150	91	34	0.7	0.7	NUM
eurjchem-1150	91	35	ml	ml	NOUN
eurjchem-1150	91	36	,	,	PUNCT
eurjchem-1150	91	37	8	8	NUM
eurjchem-1150	91	38	mmol	mmol	NOUN
eurjchem-1150	91	39	)	)	PUNCT
eurjchem-1150	91	40	in	in	ADP
eurjchem-1150	91	41	dry	dry	ADJ
eurjchem-1150	91	42	ch2cl2	ch2cl2	PUNCT
eurjchem-1150	91	43	(	(	PUNCT
eurjchem-1150	91	44	20	20	NUM
eurjchem-1150	91	45	ml	ml	NOUN
eurjchem-1150	91	46	)	)	PUNCT
eurjchem-1150	91	47	,	,	PUNCT
eurjchem-1150	91	48	dmso	dmso	NOUN
eurjchem-1150	91	49	was	be	AUX
eurjchem-1150	91	50	added	add	VERB
eurjchem-1150	91	51	drop‐wise	drop‐wise	NOUN
eurjchem-1150	91	52	(	(	PUNCT
eurjchem-1150	91	53	1.14	1.14	NUM
eurjchem-1150	91	54	ml	ml	NOUN
eurjchem-1150	91	55	,	,	PUNCT
eurjchem-1150	91	56	16	16	NUM
eurjchem-1150	91	57	mmol	mmol	NOUN
eurjchem-1150	91	58	)	)	PUNCT
eurjchem-1150	91	59	at	at	ADP
eurjchem-1150	91	60	‐78	‐78	NOUN
eurjchem-1150	91	61	°	°	ADP
eurjchem-1150	91	62	c	c	NOUN
eurjchem-1150	91	63	over	over	ADP
eurjchem-1150	91	64	20	20	NUM
eurjchem-1150	91	65	min	min	NOUN
eurjchem-1150	91	66	under	under	ADP
eurjchem-1150	91	67	nitrogen	nitrogen	NOUN
eurjchem-1150	91	68	atmosphere	atmosphere	NOUN
eurjchem-1150	91	69	and	and	CCONJ
eurjchem-1150	91	70	stirred	stir	VERB
eurjchem-1150	91	71	for	for	ADP
eurjchem-1150	91	72	30	30	NUM
eurjchem-1150	91	73	min	min	NOUN
eurjchem-1150	91	74	at	at	ADP
eurjchem-1150	91	75	the	the	DET
eurjchem-1150	91	76	same	same	ADJ
eurjchem-1150	91	77	temperature	temperature	NOUN
eurjchem-1150	91	78	.	.	PUNCT
eurjchem-1150	92	1	to	to	ADP
eurjchem-1150	92	2	this	this	DET
eurjchem-1150	92	3	reaction	reaction	NOUN
eurjchem-1150	92	4	mixture	mixture	NOUN
eurjchem-1150	92	5	,	,	PUNCT
eurjchem-1150	92	6	compound	compound	NOUN
eurjchem-1150	92	7	9	9	NUM
eurjchem-1150	92	8	(	(	PUNCT
eurjchem-1150	92	9	1.6	1.6	NUM
eurjchem-1150	92	10	g	g	NOUN
eurjchem-1150	92	11	,	,	PUNCT
eurjchem-1150	92	12	4	4	NUM
eurjchem-1150	92	13	mmol	mmol	NOUN
eurjchem-1150	92	14	)	)	PUNCT
eurjchem-1150	92	15	in	in	ADP
eurjchem-1150	92	16	ch2cl2	ch2cl2	X
eurjchem-1150	92	17	(	(	PUNCT
eurjchem-1150	92	18	5.0	5.0	NUM
eurjchem-1150	92	19	ml	ml	NOUN
eurjchem-1150	92	20	)	)	PUNCT
eurjchem-1150	92	21	was	be	AUX
eurjchem-1150	92	22	added	add	VERB
eurjchem-1150	92	23	drop‐wise	drop‐wise	NOUN
eurjchem-1150	92	24	over	over	ADP
eurjchem-1150	92	25	15	15	NUM
eurjchem-1150	92	26	min	min	NOUN
eurjchem-1150	92	27	at	at	ADP
eurjchem-1150	92	28	‐78	‐78	NOUN
eurjchem-1150	92	29	°	°	ADP
eurjchem-1150	92	30	c	c	NOUN
eurjchem-1150	92	31	,	,	PUNCT
eurjchem-1150	92	32	and	and	CCONJ
eurjchem-1150	92	33	resulting	result	VERB
eurjchem-1150	92	34	mixture	mixture	NOUN
eurjchem-1150	92	35	was	be	AUX
eurjchem-1150	92	36	stirred	stir	VERB
eurjchem-1150	92	37	for	for	ADP
eurjchem-1150	92	38	3	3	NUM
eurjchem-1150	92	39	h	h	NOUN
eurjchem-1150	92	40	at	at	ADP
eurjchem-1150	92	41	same	same	ADJ
eurjchem-1150	92	42	temperature	temperature	NOUN
eurjchem-1150	92	43	.	.	PUNCT
eurjchem-1150	93	1	the	the	DET
eurjchem-1150	93	2	reaction	reaction	NOUN
eurjchem-1150	93	3	was	be	AUX
eurjchem-1150	93	4	quenched	quench	VERB
eurjchem-1150	93	5	with	with	ADP
eurjchem-1150	93	6	et3n	et3n	PROPN
eurjchem-1150	93	7	(	(	PUNCT
eurjchem-1150	93	8	5.0	5.0	NUM
eurjchem-1150	93	9	ml	ml	NOUN
eurjchem-1150	93	10	)	)	PUNCT
eurjchem-1150	93	11	and	and	CCONJ
eurjchem-1150	93	12	allowed	allow	VERB
eurjchem-1150	93	13	to	to	PART
eurjchem-1150	93	14	reach	reach	VERB
eurjchem-1150	93	15	room	room	NOUN
eurjchem-1150	93	16	temperature	temperature	NOUN
eurjchem-1150	93	17	over	over	ADP
eurjchem-1150	93	18	30	30	NUM
eurjchem-1150	93	19	min	min	NOUN
eurjchem-1150	93	20	.	.	PUNCT
eurjchem-1150	94	1	the	the	DET
eurjchem-1150	94	2	solvent	solvent	NOUN
eurjchem-1150	94	3	was	be	AUX
eurjchem-1150	94	4	removed	remove	VERB
eurjchem-1150	94	5	on	on	ADP
eurjchem-1150	94	6	rotavapor	rotavapor	ADJ
eurjchem-1150	94	7	and	and	CCONJ
eurjchem-1150	94	8	the	the	DET
eurjchem-1150	94	9	residue	residue	NOUN
eurjchem-1150	94	10	was	be	AUX
eurjchem-1150	94	11	purified	purify	VERB
eurjchem-1150	94	12	by	by	ADP
eurjchem-1150	94	13	a	a	DET
eurjchem-1150	94	14	flash	flash	NOUN
eurjchem-1150	94	15	column	column	NOUN
eurjchem-1150	94	16	chromatography	chromatography	NOUN
eurjchem-1150	94	17	(	(	PUNCT
eurjchem-1150	94	18	hexane	hexane	NOUN
eurjchem-1150	94	19	:	:	PUNCT
eurjchem-1150	94	20	etoac	etoac	ADJ
eurjchem-1150	94	21	,	,	PUNCT
eurjchem-1150	94	22	10:1	10:1	NUM
eurjchem-1150	94	23	,	,	PUNCT
eurjchem-1150	94	24	v	v	NOUN
eurjchem-1150	94	25	:	:	SYM
eurjchem-1150	94	26	v	v	NOUN
eurjchem-1150	94	27	)	)	PUNCT
eurjchem-1150	94	28	to	to	PART
eurjchem-1150	94	29	obtain	obtain	VERB
eurjchem-1150	94	30	crude	crude	ADJ
eurjchem-1150	94	31	aldehyde	aldehyde	NOUN
eurjchem-1150	94	32	which	which	PRON
eurjchem-1150	94	33	was	be	AUX
eurjchem-1150	94	34	employed	employ	VERB
eurjchem-1150	94	35	in	in	ADP
eurjchem-1150	94	36	the	the	DET
eurjchem-1150	94	37	next	next	ADJ
eurjchem-1150	94	38	step	step	NOUN
eurjchem-1150	94	39	immediately	immediately	ADV
eurjchem-1150	94	40	.	.	PUNCT
eurjchem-1150	95	1	the	the	DET
eurjchem-1150	95	2	solution	solution	NOUN
eurjchem-1150	95	3	of	of	ADP
eurjchem-1150	95	4	crude	crude	ADJ
eurjchem-1150	95	5	aldehyde	aldehyde	NOUN
eurjchem-1150	95	6	(	(	PUNCT
eurjchem-1150	95	7	1.52	1.52	NUM
eurjchem-1150	95	8	g	g	NOUN
eurjchem-1150	95	9	,	,	PUNCT
eurjchem-1150	95	10	3.82	3.82	NUM
eurjchem-1150	95	11	mmol	mmol	NOUN
eurjchem-1150	95	12	)	)	PUNCT
eurjchem-1150	95	13	in	in	ADP
eurjchem-1150	95	14	meoh	meoh	PROPN
eurjchem-1150	95	15	(	(	PUNCT
eurjchem-1150	95	16	15	15	NUM
eurjchem-1150	95	17	ml	ml	NOUN
eurjchem-1150	95	18	)	)	PUNCT
eurjchem-1150	95	19	was	be	AUX
eurjchem-1150	95	20	added	add	VERB
eurjchem-1150	95	21	to	to	ADP
eurjchem-1150	95	22	a	a	DET
eurjchem-1150	95	23	solution	solution	NOUN
eurjchem-1150	95	24	of	of	ADP
eurjchem-1150	95	25	ph3p	ph3p	PROPN
eurjchem-1150	95	26	=	=	VERB
eurjchem-1150	95	27	chcooet	chcooet	ADJ
eurjchem-1150	95	28	(	(	PUNCT
eurjchem-1150	95	29	4	4	NUM
eurjchem-1150	95	30	g	g	NOUN
eurjchem-1150	95	31	,	,	PUNCT
eurjchem-1150	95	32	11.5	11.5	NUM
eurjchem-1150	95	33	mmol	mmol	NOUN
eurjchem-1150	95	34	)	)	PUNCT
eurjchem-1150	95	35	in	in	ADP
eurjchem-1150	95	36	meoh	meoh	PROPN
eurjchem-1150	95	37	(	(	PUNCT
eurjchem-1150	95	38	100	100	NUM
eurjchem-1150	95	39	ml	ml	NOUN
eurjchem-1150	95	40	)	)	PUNCT
eurjchem-1150	95	41	at	at	ADP
eurjchem-1150	95	42	‐50	‐50	NOUN
eurjchem-1150	95	43	°	°	ADP
eurjchem-1150	95	44	c	c	NOUN
eurjchem-1150	95	45	drop‐wise	drop‐wise	VERB
eurjchem-1150	95	46	over	over	ADP
eurjchem-1150	95	47	30	30	NUM
eurjchem-1150	95	48	min	min	NOUN
eurjchem-1150	95	49	.	.	PUNCT
eurjchem-1150	96	1	the	the	DET
eurjchem-1150	96	2	resulting	result	VERB
eurjchem-1150	96	3	solution	solution	NOUN
eurjchem-1150	96	4	was	be	AUX
eurjchem-1150	96	5	stirred	stir	VERB
eurjchem-1150	96	6	for	for	ADP
eurjchem-1150	96	7	1	1	NUM
eurjchem-1150	96	8	h	h	NOUN
eurjchem-1150	96	9	at	at	ADP
eurjchem-1150	96	10	same	same	ADJ
eurjchem-1150	96	11	temperature	temperature	NOUN
eurjchem-1150	96	12	,	,	PUNCT
eurjchem-1150	96	13	diluted	dilute	VERB
eurjchem-1150	96	14	with	with	ADP
eurjchem-1150	96	15	water	water	NOUN
eurjchem-1150	96	16	and	and	CCONJ
eurjchem-1150	96	17	extracted	extract	VERB
eurjchem-1150	96	18	with	with	ADP
eurjchem-1150	96	19	ch2cl2	ch2cl2	X
eurjchem-1150	96	20	(	(	PUNCT
eurjchem-1150	96	21	3×25	3×25	NUM
eurjchem-1150	96	22	ml	ml	NOUN
eurjchem-1150	96	23	)	)	PUNCT
eurjchem-1150	96	24	.	.	PUNCT
eurjchem-1150	97	1	the	the	DET
eurjchem-1150	97	2	organic	organic	ADJ
eurjchem-1150	97	3	layer	layer	NOUN
eurjchem-1150	97	4	was	be	AUX
eurjchem-1150	97	5	dried	dry	VERB
eurjchem-1150	97	6	over	over	ADP
eurjchem-1150	97	7	anhydrous	anhydrous	ADJ
eurjchem-1150	97	8	mgso4	mgso4	NOUN
eurjchem-1150	97	9	and	and	CCONJ
eurjchem-1150	97	10	the	the	DET
eurjchem-1150	97	11	solvent	solvent	NOUN
eurjchem-1150	97	12	was	be	AUX
eurjchem-1150	97	13	removed	remove	VERB
eurjchem-1150	97	14	under	under	ADP
eurjchem-1150	97	15	vacuum	vacuum	NOUN
eurjchem-1150	97	16	.	.	PUNCT
eurjchem-1150	98	1	the	the	DET
eurjchem-1150	98	2	residue	residue	NOUN
eurjchem-1150	98	3	was	be	AUX
eurjchem-1150	98	4	purified	purify	VERB
eurjchem-1150	98	5	by	by	ADP
eurjchem-1150	98	6	flash	flash	NOUN
eurjchem-1150	98	7	column	column	NOUN
eurjchem-1150	98	8	chromatography	chromatography	NOUN
eurjchem-1150	98	9	(	(	PUNCT
eurjchem-1150	98	10	hexane	hexane	NOUN
eurjchem-1150	98	11	:	:	PUNCT
eurjchem-1150	98	12	etoac	etoac	ADJ
eurjchem-1150	98	13	,	,	PUNCT
eurjchem-1150	98	14	50:1	50:1	NUM
eurjchem-1150	98	15	,	,	PUNCT
eurjchem-1150	98	16	v	v	NOUN
eurjchem-1150	98	17	:	:	SYM
eurjchem-1150	98	18	v	v	NOUN
eurjchem-1150	98	19	)	)	PUNCT
eurjchem-1150	98	20	to	to	PART
eurjchem-1150	98	21	obtain	obtain	VERB
eurjchem-1150	98	22	pure	pure	ADJ
eurjchem-1150	98	23	compounds	compound	NOUN
eurjchem-1150	98	24	10a	10a	NOUN
eurjchem-1150	98	25	and	and	CCONJ
eurjchem-1150	98	26	10b	10b	NOUN
eurjchem-1150	98	27	in	in	ADP
eurjchem-1150	98	28	80:20	80:20	NUM
eurjchem-1150	98	29	ratio	ratio	NOUN
eurjchem-1150	98	30	(	(	PUNCT
eurjchem-1150	98	31	scheme	scheme	NOUN
eurjchem-1150	98	32	1	1	NUM
eurjchem-1150	98	33	)	)	PUNCT
eurjchem-1150	98	34	.	.	PUNCT
eurjchem-1150	99	1	(	(	PUNCT
eurjchem-1150	99	2	z)‐ethyl	z)‐ethyl	PROPN
eurjchem-1150	99	3	3‐((4s,5s)‐5‐((tert‐butyldiphenylsilyloxy)methyl)‐	3‐((4s,5s)‐5‐((tert‐butyldiphenylsilyloxy)methyl)‐	NUM
eurjchem-1150	99	4	2,2‐dimethyl‐1,3‐dioxolan	2,2‐dimethyl‐1,3‐dioxolan	NUM
eurjchem-1150	99	5	‐4‐yl)acrylate	‐4‐yl)acrylate	PROPN
eurjchem-1150	99	6	(	(	PUNCT
eurjchem-1150	99	7	10a	10a	NUM
eurjchem-1150	99	8	):	):	PUNCT
eurjchem-1150	99	9	color	color	NOUN
eurjchem-1150	99	10	:	:	PUNCT
eurjchem-1150	99	11	colorless	colorless	ADJ
eurjchem-1150	99	12	oil	oil	NOUN
eurjchem-1150	99	13	.	.	PUNCT
eurjchem-1150	100	1	yield	yield	NOUN
eurjchem-1150	100	2	:	:	PUNCT
eurjchem-1150	100	3	1.32	1.32	NUM
eurjchem-1150	100	4	g	g	NOUN
eurjchem-1150	100	5	,	,	PUNCT
eurjchem-1150	100	6	70	70	NUM
eurjchem-1150	100	7	%	%	NOUN
eurjchem-1150	100	8	.	.	PUNCT
eurjchem-1150	101	1	ft‐ir	ft‐ir	NOUN
eurjchem-1150	101	2	(	(	PUNCT
eurjchem-1150	101	3	neat	neat	ADJ
eurjchem-1150	101	4	,	,	PUNCT
eurjchem-1150	101	5	ν	ν	NOUN
eurjchem-1150	101	6	,	,	PUNCT
eurjchem-1150	101	7	cm‐1	cm‐1	PROPN
eurjchem-1150	101	8	):	):	PUNCT
eurjchem-1150	101	9	2932	2932	NUM
eurjchem-1150	101	10	,	,	PUNCT
eurjchem-1150	101	11	1720	1720	NUM
eurjchem-1150	101	12	,	,	PUNCT
eurjchem-1150	101	13	1111	1111	NUM
eurjchem-1150	101	14	.	.	PUNCT
eurjchem-1150	102	1	1h	1h	NUM
eurjchem-1150	102	2	nmr	nmr	NOUN
eurjchem-1150	102	3	(	(	PUNCT
eurjchem-1150	102	4	300	300	NUM
eurjchem-1150	102	5	mhz	mhz	NOUN
eurjchem-1150	102	6	,	,	PUNCT
eurjchem-1150	102	7	cdcl3	cdcl3	PROPN
eurjchem-1150	102	8	,	,	PUNCT
eurjchem-1150	102	9	δ	δ	PROPN
eurjchem-1150	102	10	,	,	PUNCT
eurjchem-1150	102	11	ppm	ppm	NOUN
eurjchem-1150	102	12	):	):	PUNCT
eurjchem-1150	102	13	1.04	1.04	NUM
eurjchem-1150	102	14	(	(	PUNCT
eurjchem-1150	102	15	s	s	PROPN
eurjchem-1150	102	16	,	,	PUNCT
eurjchem-1150	102	17	9h	9h	NUM
eurjchem-1150	102	18	,	,	PUNCT
eurjchem-1150	102	19	(	(	PUNCT
eurjchem-1150	102	20	ch3)3c‐si	ch3)3c‐si	PROPN
eurjchem-1150	102	21	)	)	PUNCT
eurjchem-1150	102	22	,	,	PUNCT
eurjchem-1150	102	23	1.21	1.21	NUM
eurjchem-1150	102	24	(	(	PUNCT
eurjchem-1150	102	25	t	t	PROPN
eurjchem-1150	102	26	,	,	PUNCT
eurjchem-1150	102	27	3h	3h	NUM
eurjchem-1150	102	28	,	,	PUNCT
eurjchem-1150	102	29	ch3‐ch2‐o	ch3‐ch2‐o	NOUN
eurjchem-1150	102	30	)	)	PUNCT
eurjchem-1150	102	31	,	,	PUNCT
eurjchem-1150	102	32	1.432	1.432	NUM
eurjchem-1150	102	33	(	(	PUNCT
eurjchem-1150	102	34	s	s	PROPN
eurjchem-1150	102	35	,	,	PUNCT
eurjchem-1150	102	36	3h	3h	NUM
eurjchem-1150	102	37	,	,	PUNCT
eurjchem-1150	102	38	ch3‐c‐o	ch3‐c‐o	PROPN
eurjchem-1150	102	39	)	)	PUNCT
eurjchem-1150	102	40	,	,	PUNCT
eurjchem-1150	102	41	1.439	1.439	NUM
eurjchem-1150	102	42	(	(	PUNCT
eurjchem-1150	102	43	s	s	PROPN
eurjchem-1150	102	44	,	,	PUNCT
eurjchem-1150	102	45	3h	3h	NUM
eurjchem-1150	102	46	,	,	PUNCT
eurjchem-1150	102	47	ch3‐c‐o	ch3‐c‐o	PROPN
eurjchem-1150	102	48	)	)	PUNCT
eurjchem-1150	102	49	,	,	PUNCT
eurjchem-1150	102	50	3.80‐3.88	3.80‐3.88	NUM
eurjchem-1150	102	51	(	(	PUNCT
eurjchem-1150	102	52	m	m	PROPN
eurjchem-1150	102	53	,	,	PUNCT
eurjchem-1150	102	54	3h	3h	NUM
eurjchem-1150	102	55	,	,	PUNCT
eurjchem-1150	102	56	ch2‐osi	ch2‐osi	PROPN
eurjchem-1150	102	57	,	,	PUNCT
eurjchem-1150	102	58	ch‐ch2‐osi	ch‐ch2‐osi	NOUN
eurjchem-1150	102	59	)	)	PUNCT
eurjchem-1150	102	60	,	,	PUNCT
eurjchem-1150	102	61	4.07	4.07	NUM
eurjchem-1150	102	62	(	(	PUNCT
eurjchem-1150	102	63	q	q	NOUN
eurjchem-1150	102	64	,	,	PUNCT
eurjchem-1150	102	65	2h	2h	NUM
eurjchem-1150	102	66	,	,	PUNCT
eurjchem-1150	102	67	ch2‐oco	ch2‐oco	PROPN
eurjchem-1150	102	68	)	)	PUNCT
eurjchem-1150	102	69	,	,	PUNCT
eurjchem-1150	102	70	5.44‐5.52	5.44‐5.52	NUM
eurjchem-1150	102	71	(	(	PUNCT
eurjchem-1150	102	72	m	m	PROPN
eurjchem-1150	102	73	,	,	PUNCT
eurjchem-1150	102	74	1h	1h	NUM
eurjchem-1150	102	75	,	,	PUNCT
eurjchem-1150	102	76	ch‐ch	ch‐ch	ADJ
eurjchem-1150	102	77	=	=	NOUN
eurjchem-1150	102	78	ch	ch	NOUN
eurjchem-1150	102	79	)	)	PUNCT
eurjchem-1150	102	80	,	,	PUNCT
eurjchem-1150	102	81	5.86	5.86	NUM
eurjchem-1150	102	82	(	(	PUNCT
eurjchem-1150	102	83	dd	dd	NOUN
eurjchem-1150	102	84	,	,	PUNCT
eurjchem-1150	102	85	1h	1h	NUM
eurjchem-1150	102	86	,	,	PUNCT
eurjchem-1150	102	87	j	j	PROPN
eurjchem-1150	102	88	=	=	SYM
eurjchem-1150	102	89	10.5	10.5	NUM
eurjchem-1150	102	90	,	,	PUNCT
eurjchem-1150	102	91	1.5	1.5	NUM
eurjchem-1150	102	92	hz	hz	ADJ
eurjchem-1150	102	93	,	,	PUNCT
eurjchem-1150	102	94	hc‐coo	hc‐coo	NOUN
eurjchem-1150	102	95	)	)	PUNCT
eurjchem-1150	102	96	,	,	PUNCT
eurjchem-1150	102	97	6.12	6.12	NUM
eurjchem-1150	102	98	(	(	PUNCT
eurjchem-1150	102	99	dd	dd	PROPN
eurjchem-1150	102	100	,	,	PUNCT
eurjchem-1150	102	101	1h	1h	NUM
eurjchem-1150	102	102	,	,	PUNCT
eurjchem-1150	102	103	j	j	PROPN
eurjchem-1150	102	104	=	=	SYM
eurjchem-1150	102	105	9.0	9.0	NUM
eurjchem-1150	102	106	,	,	PUNCT
eurjchem-1150	102	107	3.0	3.0	NUM
eurjchem-1150	102	108	hz	hz	NOUN
eurjchem-1150	102	109	,	,	PUNCT
eurjchem-1150	102	110	hc	hc	PROPN
eurjchem-1150	102	111	=	=	NOUN
eurjchem-1150	102	112	ch‐coo	ch‐coo	NOUN
eurjchem-1150	102	113	)	)	PUNCT
eurjchem-1150	102	114	,	,	PUNCT
eurjchem-1150	102	115	7.32‐7.43	7.32‐7.43	NUM
eurjchem-1150	102	116	(	(	PUNCT
eurjchem-1150	102	117	m	m	PROPN
eurjchem-1150	102	118	,	,	PUNCT
eurjchem-1150	102	119	6h	6h	NUM
eurjchem-1150	102	120	,	,	PUNCT
eurjchem-1150	102	121	ar‐h	ar‐h	PROPN
eurjchem-1150	102	122	)	)	PUNCT
eurjchem-1150	102	123	,	,	PUNCT
eurjchem-1150	102	124	7.67‐7.69	7.67‐7.69	NUM
eurjchem-1150	102	125	(	(	PUNCT
eurjchem-1150	102	126	m	m	PROPN
eurjchem-1150	102	127	,	,	PUNCT
eurjchem-1150	102	128	4h	4h	NOUN
eurjchem-1150	102	129	,	,	PUNCT
eurjchem-1150	102	130	ar‐h	ar‐h	PROPN
eurjchem-1150	102	131	)	)	PUNCT
eurjchem-1150	102	132	.	.	PUNCT
eurjchem-1150	103	1	13c	13c	NOUN
eurjchem-1150	103	2	nmr	nmr	NOUN
eurjchem-1150	103	3	(	(	PUNCT
eurjchem-1150	103	4	75	75	NUM
eurjchem-1150	103	5	mhz	mhz	NOUN
eurjchem-1150	103	6	,	,	PUNCT
eurjchem-1150	103	7	cdcl3	cdcl3	PROPN
eurjchem-1150	103	8	,	,	PUNCT
eurjchem-1150	103	9	δ	δ	PROPN
eurjchem-1150	103	10	,	,	PUNCT
eurjchem-1150	103	11	ppm	ppm	NUM
eurjchem-1150	103	12	):	):	PUNCT
eurjchem-1150	103	13	14.1	14.1	NUM
eurjchem-1150	103	14	,	,	PUNCT
eurjchem-1150	103	15	19.1	19.1	NUM
eurjchem-1150	103	16	,	,	PUNCT
eurjchem-1150	103	17	26.7	26.7	NUM
eurjchem-1150	103	18	,	,	PUNCT
eurjchem-1150	103	19	27.0	27.0	NUM
eurjchem-1150	103	20	,	,	PUNCT
eurjchem-1150	103	21	27.1	27.1	NUM
eurjchem-1150	103	22	,	,	PUNCT
eurjchem-1150	103	23	60.3	60.3	NUM
eurjchem-1150	103	24	,	,	PUNCT
eurjchem-1150	103	25	64.1	64.1	NUM
eurjchem-1150	103	26	,	,	PUNCT
eurjchem-1150	103	27	73.4	73.4	NUM
eurjchem-1150	103	28	,	,	PUNCT
eurjchem-1150	103	29	82.1	82.1	NUM
eurjchem-1150	103	30	,	,	PUNCT
eurjchem-1150	103	31	117.0	117.0	NUM
eurjchem-1150	103	32	,	,	PUNCT
eurjchem-1150	103	33	122.9	122.9	NUM
eurjchem-1150	103	34	,	,	PUNCT
eurjchem-1150	103	35	127.5	127.5	NUM
eurjchem-1150	103	36	,	,	PUNCT
eurjchem-1150	103	37	127.7	127.7	NUM
eurjchem-1150	103	38	,	,	PUNCT
eurjchem-1150	103	39	129.5	129.5	NUM
eurjchem-1150	103	40	,	,	PUNCT
eurjchem-1150	103	41	130	130	NUM
eurjchem-1150	103	42	,	,	PUNCT
eurjchem-1150	103	43	135.6	135.6	NUM
eurjchem-1150	103	44	,	,	PUNCT
eurjchem-1150	103	45	135.7	135.7	NUM
eurjchem-1150	103	46	,	,	PUNCT
eurjchem-1150	103	47	145.3	145.3	NUM
eurjchem-1150	103	48	,	,	PUNCT
eurjchem-1150	103	49	(	(	PUNCT
eurjchem-1150	103	50	c	c	X
eurjchem-1150	103	51	=	=	NOUN
eurjchem-1150	103	52	o	o	X
eurjchem-1150	103	53	not	not	PART
eurjchem-1150	103	54	seen	see	VERB
eurjchem-1150	103	55	)	)	PUNCT
eurjchem-1150	103	56	.	.	PUNCT
eurjchem-1150	104	1	esi‐ms	esi‐ms	PROPN
eurjchem-1150	104	2	(	(	PUNCT
eurjchem-1150	104	3	m	m	PROPN
eurjchem-1150	104	4	/	/	SYM
eurjchem-1150	104	5	z	z	NOUN
eurjchem-1150	104	6	):	):	PUNCT
eurjchem-1150	104	7	469	469	NUM
eurjchem-1150	104	8	(	(	PUNCT
eurjchem-1150	104	9	m+1)+	m+1)+	NOUN
eurjchem-1150	104	10	,	,	PUNCT
eurjchem-1150	104	11	491	491	NUM
eurjchem-1150	104	12	(	(	PUNCT
eurjchem-1150	104	13	m+na)+	m+na)+	PROPN
eurjchem-1150	104	14	.	.	PUNCT
eurjchem-1150	105	1	(	(	PUNCT
eurjchem-1150	105	2	e)‐ethyl	e)‐ethyl	PROPN
eurjchem-1150	105	3	3‐((4s,5s)‐5‐((tert‐butyldiphenylsilyloxy	3‐((4s,5s)‐5‐((tert‐butyldiphenylsilyloxy	NUM
eurjchem-1150	105	4	)	)	PUNCT
eurjchem-1150	105	5	methyl)‐	methyl)‐	PROPN
eurjchem-1150	105	6	2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)acrylate	2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)acrylate	NUM
eurjchem-1150	105	7	(	(	PUNCT
eurjchem-1150	105	8	10b	10b	NOUN
eurjchem-1150	105	9	):	):	PUNCT
eurjchem-1150	105	10	color	color	NOUN
eurjchem-1150	105	11	:	:	PUNCT
eurjchem-1150	105	12	colorless	colorless	ADJ
eurjchem-1150	105	13	oil	oil	NOUN
eurjchem-1150	105	14	.	.	PUNCT
eurjchem-1150	106	1	yield	yield	NOUN
eurjchem-1150	106	2	:	:	PUNCT
eurjchem-1150	106	3	0.33	0.33	NUM
eurjchem-1150	106	4	g	g	NOUN
eurjchem-1150	106	5	,	,	PUNCT
eurjchem-1150	106	6	18	18	NUM
eurjchem-1150	106	7	%	%	NOUN
eurjchem-1150	106	8	.	.	PUNCT
eurjchem-1150	107	1	ft‐ir	ft‐ir	NOUN
eurjchem-1150	107	2	(	(	PUNCT
eurjchem-1150	107	3	neat	neat	ADJ
eurjchem-1150	107	4	,	,	PUNCT
eurjchem-1150	107	5	ν	ν	NOUN
eurjchem-1150	107	6	,	,	PUNCT
eurjchem-1150	107	7	cm‐1	cm‐1	PROPN
eurjchem-1150	107	8	):	):	PUNCT
eurjchem-1150	107	9	2933	2933	NUM
eurjchem-1150	107	10	,	,	PUNCT
eurjchem-1150	107	11	1719	1719	NUM
eurjchem-1150	107	12	,	,	PUNCT
eurjchem-1150	107	13	1112	1112	NUM
eurjchem-1150	107	14	.	.	PUNCT
eurjchem-1150	108	1	1h	1h	NUM
eurjchem-1150	108	2	nmr	nmr	NOUN
eurjchem-1150	108	3	(	(	PUNCT
eurjchem-1150	108	4	300	300	NUM
eurjchem-1150	108	5	mhz	mhz	NOUN
eurjchem-1150	108	6	,	,	PUNCT
eurjchem-1150	108	7	cdcl3	cdcl3	PROPN
eurjchem-1150	108	8	,	,	PUNCT
eurjchem-1150	108	9	δ	δ	PROPN
eurjchem-1150	108	10	,	,	PUNCT
eurjchem-1150	108	11	ppm	ppm	NUM
eurjchem-1150	108	12	):	):	PUNCT
eurjchem-1150	108	13	1.07	1.07	NUM
eurjchem-1150	108	14	(	(	PUNCT
eurjchem-1150	108	15	s	s	PROPN
eurjchem-1150	108	16	,	,	PUNCT
eurjchem-1150	108	17	9h	9h	NUM
eurjchem-1150	108	18	,	,	PUNCT
eurjchem-1150	108	19	(	(	PUNCT
eurjchem-1150	108	20	ch3)3c‐si	ch3)3c‐si	PROPN
eurjchem-1150	108	21	)	)	PUNCT
eurjchem-1150	108	22	,	,	PUNCT
eurjchem-1150	108	23	1.29	1.29	NUM
eurjchem-1150	108	24	(	(	PUNCT
eurjchem-1150	108	25	t	t	PROPN
eurjchem-1150	108	26	,	,	PUNCT
eurjchem-1150	108	27	3h	3h	NUM
eurjchem-1150	108	28	,	,	PUNCT
eurjchem-1150	108	29	ch3‐ch2‐o	ch3‐ch2‐o	NOUN
eurjchem-1150	108	30	)	)	PUNCT
eurjchem-1150	108	31	,	,	PUNCT
eurjchem-1150	108	32	1.4	1.4	NUM
eurjchem-1150	108	33	(	(	PUNCT
eurjchem-1150	108	34	s	s	PROPN
eurjchem-1150	108	35	,	,	PUNCT
eurjchem-1150	108	36	3h	3h	NUM
eurjchem-1150	108	37	,	,	PUNCT
eurjchem-1150	108	38	ch3‐c‐o	ch3‐c‐o	PROPN
eurjchem-1150	108	39	)	)	PUNCT
eurjchem-1150	108	40	,	,	PUNCT
eurjchem-1150	108	41	1.44	1.44	NUM
eurjchem-1150	108	42	(	(	PUNCT
eurjchem-1150	108	43	s	s	PROPN
eurjchem-1150	108	44	,	,	PUNCT
eurjchem-1150	108	45	3h	3h	NUM
eurjchem-1150	108	46	,	,	PUNCT
eurjchem-1150	108	47	ch3‐c‐	ch3‐c‐	ADJ
eurjchem-1150	108	48	o	o	NOUN
eurjchem-1150	108	49	)	)	PUNCT
eurjchem-1150	108	50	,	,	PUNCT
eurjchem-1150	108	51	3.81‐3.88	3.81‐3.88	NUM
eurjchem-1150	108	52	(	(	PUNCT
eurjchem-1150	108	53	m	m	PROPN
eurjchem-1150	108	54	,	,	PUNCT
eurjchem-1150	108	55	3h	3h	NUM
eurjchem-1150	108	56	,	,	PUNCT
eurjchem-1150	108	57	ch2‐osi	ch2‐osi	PROPN
eurjchem-1150	108	58	,	,	PUNCT
eurjchem-1150	108	59	ch‐ch2‐osi	ch‐ch2‐osi	NOUN
eurjchem-1150	108	60	)	)	PUNCT
eurjchem-1150	108	61	,	,	PUNCT
eurjchem-1150	108	62	4.20	4.20	NUM
eurjchem-1150	108	63	(	(	PUNCT
eurjchem-1150	108	64	q	q	NOUN
eurjchem-1150	108	65	,	,	PUNCT
eurjchem-1150	108	66	2h	2h	NUM
eurjchem-1150	108	67	,	,	PUNCT
eurjchem-1150	108	68	ch2‐	ch2‐	NOUN
eurjchem-1150	108	69	oco	oco	NOUN
eurjchem-1150	108	70	)	)	PUNCT
eurjchem-1150	108	71	,	,	PUNCT
eurjchem-1150	108	72	4.57‐4.62	4.57‐4.62	NUM
eurjchem-1150	108	73	(	(	PUNCT
eurjchem-1150	108	74	m	m	PROPN
eurjchem-1150	108	75	,	,	PUNCT
eurjchem-1150	108	76	1h	1h	NUM
eurjchem-1150	108	77	,	,	PUNCT
eurjchem-1150	108	78	ch‐ch	ch‐ch	ADJ
eurjchem-1150	108	79	=	=	NOUN
eurjchem-1150	108	80	ch	ch	NOUN
eurjchem-1150	108	81	)	)	PUNCT
eurjchem-1150	108	82	,	,	PUNCT
eurjchem-1150	108	83	6.10	6.10	NUM
eurjchem-1150	108	84	(	(	PUNCT
eurjchem-1150	108	85	dd	dd	PROPN
eurjchem-1150	108	86	,	,	PUNCT
eurjchem-1150	108	87	1h	1h	NUM
eurjchem-1150	108	88	,	,	PUNCT
eurjchem-1150	108	89	j	j	PROPN
eurjchem-1150	108	90	=	=	PROPN
eurjchem-1150	108	91	15.8	15.8	NUM
eurjchem-1150	108	92	,	,	PUNCT
eurjchem-1150	108	93	1.5	1.5	NUM
eurjchem-1150	108	94	hz	hz	ADJ
eurjchem-1150	108	95	,	,	PUNCT
eurjchem-1150	108	96	hc‐coo	hc‐coo	NOUN
eurjchem-1150	108	97	)	)	PUNCT
eurjchem-1150	108	98	,	,	PUNCT
eurjchem-1150	108	99	6.93	6.93	NUM
eurjchem-1150	108	100	(	(	PUNCT
eurjchem-1150	108	101	dd	dd	PROPN
eurjchem-1150	108	102	,	,	PUNCT
eurjchem-1150	108	103	1h	1h	NUM
eurjchem-1150	108	104	,	,	PUNCT
eurjchem-1150	108	105	j	j	PROPN
eurjchem-1150	108	106	=	=	SYM
eurjchem-1150	108	107	10.5	10.5	NUM
eurjchem-1150	108	108	,	,	PUNCT
eurjchem-1150	108	109	5.2	5.2	NUM
eurjchem-1150	108	110	hz	hz	NOUN
eurjchem-1150	108	111	,	,	PUNCT
eurjchem-1150	108	112	hc	hc	PROPN
eurjchem-1150	108	113	=	=	NOUN
eurjchem-1150	108	114	ch‐coo	ch‐coo	PROPN
eurjchem-1150	108	115	)	)	PUNCT
eurjchem-1150	108	116	,	,	PUNCT
eurjchem-1150	108	117	7.35‐	7.35‐	NUM
eurjchem-1150	108	118	7.43	7.43	NUM
eurjchem-1150	108	119	(	(	PUNCT
eurjchem-1150	108	120	m	m	PROPN
eurjchem-1150	108	121	,	,	PUNCT
eurjchem-1150	108	122	6h	6h	NUM
eurjchem-1150	108	123	,	,	PUNCT
eurjchem-1150	108	124	ar‐h	ar‐h	PROPN
eurjchem-1150	108	125	)	)	PUNCT
eurjchem-1150	108	126	,	,	PUNCT
eurjchem-1150	108	127	7.65‐7.70	7.65‐7.70	NUM
eurjchem-1150	108	128	(	(	PUNCT
eurjchem-1150	108	129	m	m	PROPN
eurjchem-1150	108	130	,	,	PUNCT
eurjchem-1150	108	131	4h	4h	NOUN
eurjchem-1150	108	132	,	,	PUNCT
eurjchem-1150	108	133	ar‐h	ar‐h	PROPN
eurjchem-1150	108	134	)	)	PUNCT
eurjchem-1150	108	135	.	.	PUNCT
eurjchem-1150	109	1	13c	13c	NOUN
eurjchem-1150	109	2	nmr	nmr	NOUN
eurjchem-1150	109	3	(	(	PUNCT
eurjchem-1150	109	4	75	75	NUM
eurjchem-1150	109	5	mhz	mhz	NOUN
eurjchem-1150	109	6	,	,	PUNCT
eurjchem-1150	109	7	cdcl3	cdcl3	PROPN
eurjchem-1150	109	8	,	,	PUNCT
eurjchem-1150	109	9	δ	δ	PROPN
eurjchem-1150	109	10	,	,	PUNCT
eurjchem-1150	109	11	ppm	ppm	NUM
eurjchem-1150	109	12	):	):	PUNCT
eurjchem-1150	109	13	14.2	14.2	NUM
eurjchem-1150	109	14	,	,	PUNCT
eurjchem-1150	109	15	19.1	19.1	NUM
eurjchem-1150	109	16	,	,	PUNCT
eurjchem-1150	109	17	26.7	26.7	NUM
eurjchem-1150	109	18	,	,	PUNCT
eurjchem-1150	109	19	26.9	26.9	NUM
eurjchem-1150	109	20	,	,	PUNCT
eurjchem-1150	109	21	27.0	27.0	NUM
eurjchem-1150	109	22	,	,	PUNCT
eurjchem-1150	109	23	60.4	60.4	NUM
eurjchem-1150	109	24	,	,	PUNCT
eurjchem-1150	109	25	63.1	63.1	NUM
eurjchem-1150	109	26	,	,	PUNCT
eurjchem-1150	109	27	77.4	77.4	NUM
eurjchem-1150	109	28	,	,	PUNCT
eurjchem-1150	109	29	80.7	80.7	NUM
eurjchem-1150	109	30	,	,	PUNCT
eurjchem-1150	109	31	109.8	109.8	NUM
eurjchem-1150	109	32	,	,	PUNCT
eurjchem-1150	109	33	122.1	122.1	NUM
eurjchem-1150	109	34	,	,	PUNCT
eurjchem-1150	109	35	127.5	127.5	NUM
eurjchem-1150	109	36	,	,	PUNCT
eurjchem-1150	109	37	127.7	127.7	NUM
eurjchem-1150	109	38	,	,	PUNCT
eurjchem-1150	109	39	129.5	129.5	NUM
eurjchem-1150	109	40	,	,	PUNCT
eurjchem-1150	109	41	129.7	129.7	NUM
eurjchem-1150	109	42	,	,	PUNCT
eurjchem-1150	109	43	132.8	132.8	NUM
eurjchem-1150	109	44	,	,	PUNCT
eurjchem-1150	109	45	135.5	135.5	NUM
eurjchem-1150	109	46	,	,	PUNCT
eurjchem-1150	109	47	135.7	135.7	NUM
eurjchem-1150	109	48	,	,	PUNCT
eurjchem-1150	109	49	144.4	144.4	NUM
eurjchem-1150	109	50	,	,	PUNCT
eurjchem-1150	109	51	165.9	165.9	NUM
eurjchem-1150	109	52	.	.	PUNCT
eurjchem-1150	110	1	esi‐ms	esi‐ms	PROPN
eurjchem-1150	110	2	(	(	PUNCT
eurjchem-1150	110	3	m	m	PROPN
eurjchem-1150	110	4	/	/	SYM
eurjchem-1150	110	5	z	z	NOUN
eurjchem-1150	110	6	):	):	PUNCT
eurjchem-1150	110	7	469	469	NUM
eurjchem-1150	110	8	(	(	PUNCT
eurjchem-1150	110	9	m+1)+	m+1)+	NOUN
eurjchem-1150	110	10	,	,	PUNCT
eurjchem-1150	110	11	491	491	NUM
eurjchem-1150	110	12	(	(	PUNCT
eurjchem-1150	110	13	m+na)+	m+na)+	NOUN
eurjchem-1150	110	14	.	.	NOUN
eurjchem-1150	110	15	2.2.5	2.2.5	NUM
eurjchem-1150	110	16	.	.	PUNCT
eurjchem-1150	111	1	synthesis	synthesis	NOUN
eurjchem-1150	111	2	of	of	ADP
eurjchem-1150	111	3	(	(	PUNCT
eurjchem-1150	111	4	z)‐1‐((4s,5s)‐5‐((tert‐butyldiphenylsilyl	z)‐1‐((4s,5s)‐5‐((tert‐butyldiphenylsilyl	NOUN
eurjchem-1150	111	5	oxy)methyl)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)hept‐1‐en‐3‐ol	oxy)methyl)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)hept‐1‐en‐3‐ol	PROPN
eurjchem-1150	111	6	(	(	PUNCT
eurjchem-1150	111	7	12	12	NUM
eurjchem-1150	111	8	)	)	PUNCT
eurjchem-1150	111	9	to	to	ADP
eurjchem-1150	111	10	a	a	DET
eurjchem-1150	111	11	stirred	stir	VERB
eurjchem-1150	111	12	solution	solution	NOUN
eurjchem-1150	111	13	of	of	ADP
eurjchem-1150	111	14	compound	compound	NOUN
eurjchem-1150	111	15	10a	10a	NOUN
eurjchem-1150	111	16	(	(	PUNCT
eurjchem-1150	111	17	2.0	2.0	NUM
eurjchem-1150	111	18	g	g	NOUN
eurjchem-1150	111	19	,	,	PUNCT
eurjchem-1150	111	20	4.27	4.27	NUM
eurjchem-1150	111	21	mmol	mmol	NOUN
eurjchem-1150	111	22	)	)	PUNCT
eurjchem-1150	111	23	in	in	ADP
eurjchem-1150	111	24	ch2cl2	ch2cl2	X
eurjchem-1150	111	25	(	(	PUNCT
eurjchem-1150	111	26	50	50	NUM
eurjchem-1150	111	27	ml	ml	NOUN
eurjchem-1150	111	28	)	)	PUNCT
eurjchem-1150	111	29	,	,	PUNCT
eurjchem-1150	111	30	diisobutylaluminium	diisobutylaluminium	NOUN
eurjchem-1150	111	31	hydride	hydride	NOUN
eurjchem-1150	111	32	(	(	PUNCT
eurjchem-1150	111	33	dibal‐h	dibal‐h	PROPN
eurjchem-1150	111	34	)	)	PUNCT
eurjchem-1150	111	35	(	(	PUNCT
eurjchem-1150	111	36	2.48	2.48	NUM
eurjchem-1150	111	37	ml	ml	NOUN
eurjchem-1150	111	38	,	,	PUNCT
eurjchem-1150	111	39	4.27	4.27	NUM
eurjchem-1150	111	40	mmol	mmol	NOUN
eurjchem-1150	111	41	)	)	PUNCT
eurjchem-1150	111	42	was	be	AUX
eurjchem-1150	111	43	added	add	VERB
eurjchem-1150	111	44	drop‐wise	drop‐wise	NOUN
eurjchem-1150	111	45	at	at	ADP
eurjchem-1150	111	46	‐78	‐78	NOUN
eurjchem-1150	111	47	°	°	ADP
eurjchem-1150	111	48	c	c	NOUN
eurjchem-1150	111	49	,	,	PUNCT
eurjchem-1150	111	50	and	and	CCONJ
eurjchem-1150	111	51	the	the	DET
eurjchem-1150	111	52	reaction	reaction	NOUN
eurjchem-1150	111	53	mixture	mixture	NOUN
eurjchem-1150	111	54	was	be	AUX
eurjchem-1150	111	55	stirred	stir	VERB
eurjchem-1150	111	56	for	for	ADP
eurjchem-1150	111	57	30	30	NUM
eurjchem-1150	111	58	min	min	NOUN
eurjchem-1150	111	59	at	at	ADP
eurjchem-1150	111	60	same	same	ADJ
eurjchem-1150	111	61	temperature	temperature	NOUN
eurjchem-1150	111	62	.	.	PUNCT
eurjchem-1150	112	1	the	the	DET
eurjchem-1150	112	2	reaction	reaction	NOUN
eurjchem-1150	112	3	was	be	AUX
eurjchem-1150	112	4	quenched	quench	VERB
eurjchem-1150	112	5	with	with	ADP
eurjchem-1150	112	6	aqueous	aqueous	ADJ
eurjchem-1150	112	7	meoh	meoh	NOUN
eurjchem-1150	112	8	(	(	PUNCT
eurjchem-1150	112	9	10	10	NUM
eurjchem-1150	112	10	ml	ml	NOUN
eurjchem-1150	112	11	,	,	PUNCT
eurjchem-1150	112	12	50	50	NUM
eurjchem-1150	112	13	%	%	NOUN
eurjchem-1150	112	14	,	,	PUNCT
eurjchem-1150	112	15	v	v	NOUN
eurjchem-1150	112	16	:	:	PUNCT
eurjchem-1150	112	17	v	v	NOUN
eurjchem-1150	112	18	)	)	PUNCT
eurjchem-1150	112	19	at	at	ADP
eurjchem-1150	112	20	0	0	NUM
eurjchem-1150	112	21	°	°	ADP
eurjchem-1150	112	22	c	c	NOUN
eurjchem-1150	112	23	.	.	PUNCT
eurjchem-1150	113	1	saturated	saturate	VERB
eurjchem-1150	113	2	sodium	sodium	NOUN
eurjchem-1150	113	3	potassium	potassium	NOUN
eurjchem-1150	113	4	tartrate	tartrate	NOUN
eurjchem-1150	113	5	solution	solution	NOUN
eurjchem-1150	113	6	(	(	PUNCT
eurjchem-1150	113	7	10	10	NUM
eurjchem-1150	113	8	ml	ml	NOUN
eurjchem-1150	113	9	)	)	PUNCT
eurjchem-1150	113	10	was	be	AUX
eurjchem-1150	113	11	added	add	VERB
eurjchem-1150	113	12	and	and	CCONJ
eurjchem-1150	113	13	the	the	DET
eurjchem-1150	113	14	contents	content	NOUN
eurjchem-1150	113	15	were	be	AUX
eurjchem-1150	113	16	extracted	extract	VERB
eurjchem-1150	113	17	with	with	ADP
eurjchem-1150	113	18	ch2cl2	ch2cl2	NOUN
eurjchem-1150	113	19	.	.	PUNCT
eurjchem-1150	114	1	the	the	DET
eurjchem-1150	114	2	combined	combine	VERB
eurjchem-1150	114	3	organic	organic	ADJ
eurjchem-1150	114	4	layer	layer	NOUN
eurjchem-1150	114	5	was	be	AUX
eurjchem-1150	114	6	dried	dry	VERB
eurjchem-1150	114	7	over	over	ADP
eurjchem-1150	114	8	anhydrous	anhydrous	ADJ
eurjchem-1150	114	9	mgso4	mgso4	NOUN
eurjchem-1150	114	10	,	,	PUNCT
eurjchem-1150	114	11	concentrated	concentrate	VERB
eurjchem-1150	114	12	under	under	ADP
eurjchem-1150	114	13	vacuum	vacuum	NOUN
eurjchem-1150	114	14	to	to	PART
eurjchem-1150	114	15	obtain	obtain	VERB
eurjchem-1150	114	16	the	the	DET
eurjchem-1150	114	17	crude	crude	ADJ
eurjchem-1150	114	18	aldehyde	aldehyde	NOUN
eurjchem-1150	114	19	11	11	NUM
eurjchem-1150	114	20	which	which	PRON
eurjchem-1150	114	21	was	be	AUX
eurjchem-1150	114	22	used	use	VERB
eurjchem-1150	114	23	in	in	ADP
eurjchem-1150	114	24	next	next	ADJ
eurjchem-1150	114	25	step	step	NOUN
eurjchem-1150	114	26	without	without	ADP
eurjchem-1150	114	27	further	further	ADJ
eurjchem-1150	114	28	purification	purification	NOUN
eurjchem-1150	114	29	.	.	PUNCT
eurjchem-1150	115	1	a	a	DET
eurjchem-1150	115	2	solution	solution	NOUN
eurjchem-1150	115	3	of	of	ADP
eurjchem-1150	115	4	n‐butyl	n‐butyl	PUNCT
eurjchem-1150	115	5	bromide	bromide	NOUN
eurjchem-1150	115	6	(	(	PUNCT
eurjchem-1150	115	7	0.92	0.92	NUM
eurjchem-1150	115	8	ml	ml	NOUN
eurjchem-1150	115	9	,	,	PUNCT
eurjchem-1150	115	10	8.54	8.54	NUM
eurjchem-1150	115	11	mmol	mmol	NOUN
eurjchem-1150	115	12	)	)	PUNCT
eurjchem-1150	115	13	in	in	ADP
eurjchem-1150	115	14	thf	thf	NOUN
eurjchem-1150	115	15	(	(	PUNCT
eurjchem-1150	115	16	5	5	NUM
eurjchem-1150	115	17	ml	ml	NOUN
eurjchem-1150	115	18	)	)	PUNCT
eurjchem-1150	115	19	was	be	AUX
eurjchem-1150	115	20	added	add	VERB
eurjchem-1150	115	21	to	to	ADP
eurjchem-1150	115	22	a	a	DET
eurjchem-1150	115	23	suspension	suspension	NOUN
eurjchem-1150	115	24	of	of	ADP
eurjchem-1150	115	25	mg	mg	PROPN
eurjchem-1150	115	26	(	(	PUNCT
eurjchem-1150	115	27	0.2	0.2	NUM
eurjchem-1150	115	28	g	g	NOUN
eurjchem-1150	115	29	,	,	PUNCT
eurjchem-1150	115	30	8.33	8.33	NUM
eurjchem-1150	115	31	mmol	mmol	NOUN
eurjchem-1150	115	32	)	)	PUNCT
eurjchem-1150	115	33	in	in	ADP
eurjchem-1150	115	34	thf	thf	NOUN
eurjchem-1150	115	35	(	(	PUNCT
eurjchem-1150	115	36	30	30	NUM
eurjchem-1150	115	37	ml	ml	NOUN
eurjchem-1150	115	38	)	)	PUNCT
eurjchem-1150	115	39	and	and	CCONJ
eurjchem-1150	115	40	refluxed	refluxe	VERB
eurjchem-1150	115	41	for	for	ADP
eurjchem-1150	115	42	20	20	NUM
eurjchem-1150	115	43	min	min	NOUN
eurjchem-1150	115	44	.	.	PUNCT
eurjchem-1150	116	1	the	the	DET
eurjchem-1150	116	2	reaction	reaction	NOUN
eurjchem-1150	116	3	mixture	mixture	NOUN
eurjchem-1150	116	4	was	be	AUX
eurjchem-1150	116	5	cooled	cool	VERB
eurjchem-1150	116	6	to	to	ADP
eurjchem-1150	116	7	0	0	NUM
eurjchem-1150	116	8	°	°	ADP
eurjchem-1150	116	9	c	c	NOUN
eurjchem-1150	116	10	and	and	CCONJ
eurjchem-1150	116	11	solution	solution	NOUN
eurjchem-1150	116	12	of	of	ADP
eurjchem-1150	116	13	crude	crude	ADJ
eurjchem-1150	116	14	aldehyde	aldehyde	NOUN
eurjchem-1150	116	15	11	11	NUM
eurjchem-1150	116	16	in	in	ADP
eurjchem-1150	116	17	thf	thf	NOUN
eurjchem-1150	116	18	(	(	PUNCT
eurjchem-1150	116	19	10	10	NUM
eurjchem-1150	116	20	ml	ml	NOUN
eurjchem-1150	116	21	)	)	PUNCT
eurjchem-1150	116	22	was	be	AUX
eurjchem-1150	116	23	added	add	VERB
eurjchem-1150	116	24	.	.	PUNCT
eurjchem-1150	117	1	after	after	ADP
eurjchem-1150	117	2	1	1	NUM
eurjchem-1150	117	3	h	h	NOUN
eurjchem-1150	117	4	the	the	DET
eurjchem-1150	117	5	reaction	reaction	NOUN
eurjchem-1150	117	6	was	be	AUX
eurjchem-1150	117	7	quenched	quench	VERB
eurjchem-1150	117	8	with	with	ADP
eurjchem-1150	117	9	aqueous	aqueous	ADJ
eurjchem-1150	117	10	nh4cl	nh4cl	NOUN
eurjchem-1150	117	11	,	,	PUNCT
eurjchem-1150	117	12	filtered	filter	VERB
eurjchem-1150	117	13	through	through	ADP
eurjchem-1150	117	14	a	a	DET
eurjchem-1150	117	15	celite	celite	NOUN
eurjchem-1150	117	16	.	.	PUNCT
eurjchem-1150	118	1	the	the	DET
eurjchem-1150	118	2	filtrate	filtrate	NOUN
eurjchem-1150	118	3	was	be	AUX
eurjchem-1150	118	4	dried	dry	VERB
eurjchem-1150	118	5	anhydrous	anhydrous	ADJ
eurjchem-1150	118	6	mgso4	mgso4	NOUN
eurjchem-1150	118	7	,	,	PUNCT
eurjchem-1150	118	8	concentrated	concentrate	VERB
eurjchem-1150	118	9	under	under	ADP
eurjchem-1150	118	10	vacuum	vacuum	NOUN
eurjchem-1150	118	11	,	,	PUNCT
eurjchem-1150	118	12	and	and	CCONJ
eurjchem-1150	118	13	purified	purify	VERB
eurjchem-1150	118	14	by	by	ADP
eurjchem-1150	118	15	flash	flash	NOUN
eurjchem-1150	118	16	column	column	NOUN
eurjchem-1150	118	17	chromatography	chromatography	NOUN
eurjchem-1150	118	18	(	(	PUNCT
eurjchem-1150	118	19	hexane	hexane	NOUN
eurjchem-1150	118	20	:	:	PUNCT
eurjchem-1150	118	21	etoac	etoac	ADJ
eurjchem-1150	118	22	,	,	PUNCT
eurjchem-1150	118	23	80:20	80:20	NUM
eurjchem-1150	118	24	,	,	PUNCT
eurjchem-1150	118	25	v	v	NOUN
eurjchem-1150	118	26	:	:	SYM
eurjchem-1150	118	27	v	v	NOUN
eurjchem-1150	118	28	)	)	PUNCT
eurjchem-1150	118	29	to	to	PART
eurjchem-1150	118	30	afford	afford	VERB
eurjchem-1150	118	31	diastereoisomeric	diastereoisomeric	ADJ
eurjchem-1150	118	32	mixture	mixture	NOUN
eurjchem-1150	118	33	of	of	ADP
eurjchem-1150	118	34	compound	compound	NOUN
eurjchem-1150	118	35	12	12	NUM
eurjchem-1150	118	36	(	(	PUNCT
eurjchem-1150	118	37	scheme	scheme	NOUN
eurjchem-1150	118	38	1	1	NUM
eurjchem-1150	118	39	)	)	PUNCT
eurjchem-1150	118	40	.	.	PUNCT
eurjchem-1150	119	1	color	color	NOUN
eurjchem-1150	119	2	:	:	PUNCT
eurjchem-1150	119	3	pale	pale	ADJ
eurjchem-1150	119	4	yellow	yellow	ADJ
eurjchem-1150	119	5	oil	oil	NOUN
eurjchem-1150	119	6	.	.	PUNCT
eurjchem-1150	120	1	yield	yield	NOUN
eurjchem-1150	120	2	:	:	PUNCT
eurjchem-1150	120	3	1.36	1.36	NUM
eurjchem-1150	120	4	g.	g.	NOUN
eurjchem-1150	120	5	66	66	NUM
eurjchem-1150	120	6	%	%	NOUN
eurjchem-1150	120	7	.	.	PUNCT
eurjchem-1150	121	1	ft‐ir	ft‐ir	NOUN
eurjchem-1150	121	2	(	(	PUNCT
eurjchem-1150	121	3	neat	neat	ADJ
eurjchem-1150	121	4	,	,	PUNCT
eurjchem-1150	121	5	ν	ν	NOUN
eurjchem-1150	121	6	,	,	PUNCT
eurjchem-1150	121	7	cm‐1	cm‐1	PROPN
eurjchem-1150	121	8	):	):	PUNCT
eurjchem-1150	121	9	3441	3441	NUM
eurjchem-1150	121	10	,	,	PUNCT
eurjchem-1150	121	11	2931	2931	NUM
eurjchem-1150	121	12	,	,	PUNCT
eurjchem-1150	121	13	1428	1428	NUM
eurjchem-1150	121	14	,	,	PUNCT
eurjchem-1150	121	15	1113	1113	NUM
eurjchem-1150	121	16	.	.	PUNCT
eurjchem-1150	122	1	1h	1h	NUM
eurjchem-1150	122	2	nmr	nmr	NOUN
eurjchem-1150	122	3	(	(	PUNCT
eurjchem-1150	122	4	300	300	NUM
eurjchem-1150	122	5	mhz	mhz	NOUN
eurjchem-1150	122	6	,	,	PUNCT
eurjchem-1150	122	7	cdcl3	cdcl3	PROPN
eurjchem-1150	122	8	,	,	PUNCT
eurjchem-1150	122	9	δ	δ	PROPN
eurjchem-1150	122	10	,	,	PUNCT
eurjchem-1150	122	11	ppm	ppm	NOUN
eurjchem-1150	122	12	):	):	PUNCT
eurjchem-1150	122	13	0.89	0.89	NUM
eurjchem-1150	122	14	(	(	PUNCT
eurjchem-1150	122	15	t	t	PROPN
eurjchem-1150	122	16	,	,	PUNCT
eurjchem-1150	122	17	3h	3h	NUM
eurjchem-1150	122	18	,	,	PUNCT
eurjchem-1150	122	19	ch3‐ch2‐	ch3‐ch2‐	NOUN
eurjchem-1150	122	20	)	)	PUNCT
eurjchem-1150	122	21	,	,	PUNCT
eurjchem-1150	122	22	1.06	1.06	NUM
eurjchem-1150	122	23	(	(	PUNCT
eurjchem-1150	122	24	s	s	PROPN
eurjchem-1150	122	25	,	,	PUNCT
eurjchem-1150	122	26	9h	9h	NUM
eurjchem-1150	122	27	,	,	PUNCT
eurjchem-1150	122	28	(	(	PUNCT
eurjchem-1150	122	29	ch3)3c‐si	ch3)3c‐si	PROPN
eurjchem-1150	122	30	)	)	PUNCT
eurjchem-1150	122	31	,	,	PUNCT
eurjchem-1150	122	32	1.23‐1.37	1.23‐1.37	PROPN
eurjchem-1150	122	33	(	(	PUNCT
eurjchem-1150	122	34	m	m	PROPN
eurjchem-1150	122	35	,	,	PUNCT
eurjchem-1150	122	36	4h	4h	NOUN
eurjchem-1150	122	37	,	,	PUNCT
eurjchem-1150	122	38	ch2‐ch2‐ch3	ch2‐ch2‐ch3	ADJ
eurjchem-1150	122	39	)	)	PUNCT
eurjchem-1150	122	40	,	,	PUNCT
eurjchem-1150	122	41	1.43	1.43	NUM
eurjchem-1150	122	42	(	(	PUNCT
eurjchem-1150	122	43	s	s	PROPN
eurjchem-1150	122	44	,	,	PUNCT
eurjchem-1150	122	45	6h	6h	NUM
eurjchem-1150	122	46	,	,	PUNCT
eurjchem-1150	122	47	(	(	PUNCT
eurjchem-1150	122	48	ch3)2c	ch3)2c	PROPN
eurjchem-1150	122	49	)	)	PUNCT
eurjchem-1150	122	50	,	,	PUNCT
eurjchem-1150	122	51	1.46‐1.53	1.46‐1.53	NUM
eurjchem-1150	122	52	(	(	PUNCT
eurjchem-1150	122	53	m	m	PROPN
eurjchem-1150	122	54	,	,	PUNCT
eurjchem-1150	122	55	2h	2h	NUM
eurjchem-1150	122	56	,	,	PUNCT
eurjchem-1150	122	57	ch2‐	ch2‐	NOUN
eurjchem-1150	122	58	(	(	PUNCT
eurjchem-1150	122	59	ch2)2‐ch3	ch2)2‐ch3	NUM
eurjchem-1150	122	60	)	)	PUNCT
eurjchem-1150	122	61	,	,	PUNCT
eurjchem-1150	122	62	3.69‐3.86	3.69‐3.86	NUM
eurjchem-1150	122	63	(	(	PUNCT
eurjchem-1150	122	64	m	m	PROPN
eurjchem-1150	122	65	,	,	PUNCT
eurjchem-1150	122	66	3h	3h	NUM
eurjchem-1150	122	67	,	,	PUNCT
eurjchem-1150	122	68	ch2‐osi	ch2‐osi	PROPN
eurjchem-1150	122	69	,	,	PUNCT
eurjchem-1150	122	70	ch‐ch2‐osi	ch‐ch2‐osi	NOUN
eurjchem-1150	122	71	)	)	PUNCT
eurjchem-1150	122	72	,	,	PUNCT
eurjchem-1150	122	73	4.09	4.09	NUM
eurjchem-1150	122	74	(	(	PUNCT
eurjchem-1150	122	75	q	q	NOUN
eurjchem-1150	122	76	,	,	PUNCT
eurjchem-1150	122	77	1h	1h	NUM
eurjchem-1150	122	78	,	,	PUNCT
eurjchem-1150	122	79	ch(oh	ch(oh	PROPN
eurjchem-1150	122	80	)	)	PUNCT
eurjchem-1150	122	81	)	)	PUNCT
eurjchem-1150	122	82	,	,	PUNCT
eurjchem-1150	122	83	4.43	4.43	NUM
eurjchem-1150	122	84	(	(	PUNCT
eurjchem-1150	122	85	t	t	PROPN
eurjchem-1150	122	86	,	,	PUNCT
eurjchem-1150	122	87	1h	1h	NUM
eurjchem-1150	122	88	,	,	PUNCT
eurjchem-1150	122	89	hc‐ch=	hc‐ch=	PROPN
eurjchem-1150	122	90	)	)	PUNCT
eurjchem-1150	122	91	,	,	PUNCT
eurjchem-1150	122	92	5.65	5.65	NUM
eurjchem-1150	122	93	(	(	PUNCT
eurjchem-1150	122	94	dd	dd	PROPN
eurjchem-1150	122	95	,	,	PUNCT
eurjchem-1150	122	96	1h	1h	NUM
eurjchem-1150	122	97	,	,	PUNCT
eurjchem-1150	122	98	j	j	PROPN
eurjchem-1150	122	99	=	=	SYM
eurjchem-1150	122	100	8.3	8.3	NUM
eurjchem-1150	122	101	,	,	PUNCT
eurjchem-1150	122	102	6.7	6.7	NUM
eurjchem-1150	122	103	hz	hz	NOUN
eurjchem-1150	122	104	,	,	PUNCT
eurjchem-1150	122	105	=	=	NOUN
eurjchem-1150	122	106	ch‐ch(oh	ch‐ch(oh	NOUN
eurjchem-1150	122	107	)	)	PUNCT
eurjchem-1150	122	108	)	)	PUNCT
eurjchem-1150	122	109	,	,	PUNCT
eurjchem-1150	122	110	5.78	5.78	NUM
eurjchem-1150	122	111	(	(	PUNCT
eurjchem-1150	122	112	dd	dd	PROPN
eurjchem-1150	122	113	,	,	PUNCT
eurjchem-1150	122	114	1h	1h	NUM
eurjchem-1150	122	115	,	,	PUNCT
eurjchem-1150	122	116	j	j	PROPN
eurjchem-1150	122	117	=	=	SYM
eurjchem-1150	122	118	9.8	9.8	NUM
eurjchem-1150	122	119	,	,	PUNCT
eurjchem-1150	122	120	6.0	6.0	NUM
eurjchem-1150	122	121	hz	hz	NOUN
eurjchem-1150	122	122	,	,	PUNCT
eurjchem-1150	122	123	ch	ch	NOUN
eurjchem-1150	122	124	=	=	NOUN
eurjchem-1150	122	125	ch‐ch(oh	ch‐ch(oh	NOUN
eurjchem-1150	122	126	)	)	PUNCT
eurjchem-1150	122	127	)	)	PUNCT
eurjchem-1150	122	128	,	,	PUNCT
eurjchem-1150	123	1	7.35‐7.43	7.35‐7.43	NUM
eurjchem-1150	123	2	(	(	PUNCT
eurjchem-1150	123	3	m	m	PROPN
eurjchem-1150	123	4	,	,	PUNCT
eurjchem-1150	123	5	6h	6h	NUM
eurjchem-1150	123	6	,	,	PUNCT
eurjchem-1150	123	7	ar‐h	ar‐h	PROPN
eurjchem-1150	123	8	)	)	PUNCT
eurjchem-1150	123	9	,	,	PUNCT
eurjchem-1150	123	10	7.65‐7.70	7.65‐7.70	NUM
eurjchem-1150	123	11	(	(	PUNCT
eurjchem-1150	123	12	m	m	PROPN
eurjchem-1150	123	13	,	,	PUNCT
eurjchem-1150	123	14	4h	4h	NOUN
eurjchem-1150	123	15	,	,	PUNCT
eurjchem-1150	123	16	ar‐h	ar‐h	PROPN
eurjchem-1150	123	17	)	)	PUNCT
eurjchem-1150	123	18	.	.	PUNCT
eurjchem-1150	124	1	13c	13c	NOUN
eurjchem-1150	124	2	nmr	nmr	NOUN
eurjchem-1150	124	3	(	(	PUNCT
eurjchem-1150	124	4	75	75	NUM
eurjchem-1150	124	5	mhz	mhz	NOUN
eurjchem-1150	124	6	,	,	PUNCT
eurjchem-1150	124	7	cdcl3	cdcl3	PROPN
eurjchem-1150	124	8	,	,	PUNCT
eurjchem-1150	124	9	δ	δ	PROPN
eurjchem-1150	124	10	,	,	PUNCT
eurjchem-1150	124	11	ppm	ppm	NUM
eurjchem-1150	124	12	):	):	PUNCT
eurjchem-1150	124	13	13.9	13.9	NUM
eurjchem-1150	124	14	,	,	PUNCT
eurjchem-1150	124	15	19.2	19.2	NUM
eurjchem-1150	124	16	,	,	PUNCT
eurjchem-1150	124	17	22.5	22.5	NUM
eurjchem-1150	124	18	,	,	PUNCT
eurjchem-1150	124	19	26.7	26.7	NUM
eurjchem-1150	124	20	,	,	PUNCT
eurjchem-1150	124	21	26.9	26.9	NUM
eurjchem-1150	124	22	,	,	PUNCT
eurjchem-1150	124	23	27.0	27.0	NUM
eurjchem-1150	124	24	,	,	PUNCT
eurjchem-1150	124	25	27.4	27.4	NUM
eurjchem-1150	124	26	,	,	PUNCT
eurjchem-1150	124	27	36.6	36.6	NUM
eurjchem-1150	124	28	,	,	PUNCT
eurjchem-1150	124	29	62.7	62.7	NUM
eurjchem-1150	124	30	,	,	PUNCT
eurjchem-1150	124	31	71.9	71.9	NUM
eurjchem-1150	124	32	,	,	PUNCT
eurjchem-1150	124	33	78.0	78.0	NUM
eurjchem-1150	124	34	,	,	PUNCT
eurjchem-1150	124	35	81.4	81.4	NUM
eurjchem-1150	124	36	,	,	PUNCT
eurjchem-1150	124	37	109.0	109.0	NUM
eurjchem-1150	124	38	,	,	PUNCT
eurjchem-1150	124	39	127.4	127.4	NUM
eurjchem-1150	124	40	,	,	PUNCT
eurjchem-1150	124	41	127.6	127.6	NUM
eurjchem-1150	124	42	,	,	PUNCT
eurjchem-1150	124	43	129.6	129.6	NUM
eurjchem-1150	124	44	,	,	PUNCT
eurjchem-1150	124	45	129.7	129.7	NUM
eurjchem-1150	124	46	,	,	PUNCT
eurjchem-1150	124	47	133.1	133.1	NUM
eurjchem-1150	124	48	,	,	PUNCT
eurjchem-1150	124	49	135.6	135.6	NUM
eurjchem-1150	124	50	,	,	PUNCT
eurjchem-1150	124	51	137.5	137.5	NUM
eurjchem-1150	124	52	.	.	PUNCT
eurjchem-1150	125	1	esi‐ms	esi‐ms	PROPN
eurjchem-1150	125	2	(	(	PUNCT
eurjchem-1150	125	3	m	m	PROPN
eurjchem-1150	125	4	/	/	SYM
eurjchem-1150	125	5	z	z	NOUN
eurjchem-1150	125	6	):	):	PUNCT
eurjchem-1150	125	7	505	505	NUM
eurjchem-1150	125	8	(	(	PUNCT
eurjchem-1150	125	9	m+na)+	m+na)+	PROPN
eurjchem-1150	125	10	.	.	PROPN
eurjchem-1150	125	11	hrms	hrm	VERB
eurjchem-1150	125	12	calcd	calcd	NOUN
eurjchem-1150	125	13	.	.	PUNCT
eurjchem-1150	126	1	for	for	ADP
eurjchem-1150	126	2	c29h42o4nasi	c29h42o4nasi	NOUN
eurjchem-1150	126	3	[	[	X
eurjchem-1150	126	4	m+na]+	m+na]+	NOUN
eurjchem-1150	126	5	:	:	PUNCT
eurjchem-1150	126	6	505.27446	505.27446	NUM
eurjchem-1150	126	7	,	,	PUNCT
eurjchem-1150	126	8	found	find	VERB
eurjchem-1150	126	9	:	:	PUNCT
eurjchem-1150	126	10	505.27282	505.27282	NUM
eurjchem-1150	126	11	.	.	PUNCT
eurjchem-1150	127	1	2.2.6	2.2.6	NUM
eurjchem-1150	127	2	.	.	PUNCT
eurjchem-1150	128	1	synthesis	synthesis	NOUN
eurjchem-1150	128	2	of	of	ADP
eurjchem-1150	128	3	(	(	PUNCT
eurjchem-1150	128	4	z)‐1‐((4s,5s)‐5‐((tert‐butyldiphenylsilyl	z)‐1‐((4s,5s)‐5‐((tert‐butyldiphenylsilyl	PROPN
eurjchem-1150	128	5	oxy)methyl)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)hept‐1‐en‐3‐yl	oxy)methyl)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)hept‐1‐en‐3‐yl	PROPN
eurjchem-1150	128	6	acetate	acetate	PROPN
eurjchem-1150	128	7	(	(	PUNCT
eurjchem-1150	128	8	13	13	NUM
eurjchem-1150	128	9	)	)	PUNCT
eurjchem-1150	128	10	to	to	ADP
eurjchem-1150	128	11	a	a	DET
eurjchem-1150	128	12	stirred	stir	VERB
eurjchem-1150	128	13	solution	solution	NOUN
eurjchem-1150	128	14	of	of	ADP
eurjchem-1150	128	15	alcohol	alcohol	NOUN
eurjchem-1150	128	16	12	12	NUM
eurjchem-1150	128	17	(	(	PUNCT
eurjchem-1150	128	18	482	482	NUM
eurjchem-1150	128	19	mg	mg	NOUN
eurjchem-1150	128	20	,	,	PUNCT
eurjchem-1150	128	21	1.03	1.03	NUM
eurjchem-1150	128	22	mmol	mmol	NOUN
eurjchem-1150	128	23	)	)	PUNCT
eurjchem-1150	128	24	in	in	ADP
eurjchem-1150	128	25	ch2c12	ch2c12	PROPN
eurjchem-1150	128	26	(	(	PUNCT
eurjchem-1150	128	27	10	10	NUM
eurjchem-1150	128	28	ml	ml	NOUN
eurjchem-1150	128	29	)	)	PUNCT
eurjchem-1150	128	30	were	be	AUX
eurjchem-1150	128	31	added	add	VERB
eurjchem-1150	128	32	catalytic	catalytic	ADJ
eurjchem-1150	128	33	amount	amount	NOUN
eurjchem-1150	128	34	(	(	PUNCT
eurjchem-1150	128	35	5	5	NUM
eurjchem-1150	128	36	mg	mg	NOUN
eurjchem-1150	128	37	)	)	PUNCT
eurjchem-1150	128	38	of	of	ADP
eurjchem-1150	128	39	4‐	4‐	PROPN
eurjchem-1150	128	40	dimethylaminopyridine	dimethylaminopyridine	PROPN
eurjchem-1150	128	41	(	(	PUNCT
eurjchem-1150	128	42	dmap	dmap	NOUN
eurjchem-1150	128	43	)	)	PUNCT
eurjchem-1150	128	44	and	and	CCONJ
eurjchem-1150	128	45	pyridine	pyridine	NOUN
eurjchem-1150	128	46	(	(	PUNCT
eurjchem-1150	128	47	0.126	0.126	NUM
eurjchem-1150	128	48	ml	ml	NOUN
eurjchem-1150	128	49	,	,	PUNCT
eurjchem-1150	128	50	1.55	1.55	NUM
eurjchem-1150	128	51	mmol	mmol	NOUN
eurjchem-1150	128	52	)	)	PUNCT
eurjchem-1150	128	53	at	at	ADP
eurjchem-1150	128	54	0	0	NUM
eurjchem-1150	128	55	°	°	ADP
eurjchem-1150	128	56	c	c	NOUN
eurjchem-1150	128	57	.	.	PUNCT
eurjchem-1150	129	1	under	under	ADP
eurjchem-1150	129	2	stirring	stir	VERB
eurjchem-1150	129	3	at	at	ADP
eurjchem-1150	129	4	same	same	ADJ
eurjchem-1150	129	5	temperature	temperature	NOUN
eurjchem-1150	129	6	,	,	PUNCT
eurjchem-1150	129	7	acetic	acetic	ADJ
eurjchem-1150	129	8	anhydride	anhydride	NOUN
eurjchem-1150	129	9	(	(	PUNCT
eurjchem-1150	129	10	0.147	0.147	NUM
eurjchem-1150	129	11	ml	ml	NOUN
eurjchem-1150	129	12	,	,	PUNCT
eurjchem-1150	129	13	1.55	1.55	NUM
eurjchem-1150	129	14	mmol	mmol	NOUN
eurjchem-1150	129	15	)	)	PUNCT
eurjchem-1150	129	16	was	be	AUX
eurjchem-1150	129	17	added	add	VERB
eurjchem-1150	129	18	and	and	CCONJ
eurjchem-1150	129	19	the	the	DET
eurjchem-1150	129	20	resulting	result	VERB
eurjchem-1150	129	21	mixture	mixture	NOUN
eurjchem-1150	129	22	was	be	AUX
eurjchem-1150	129	23	stirred	stir	VERB
eurjchem-1150	129	24	for	for	ADP
eurjchem-1150	129	25	3	3	NUM
eurjchem-1150	129	26	h	h	NOUN
eurjchem-1150	129	27	at	at	ADP
eurjchem-1150	129	28	room	room	NOUN
eurjchem-1150	129	29	temperature	temperature	NOUN
eurjchem-1150	129	30	.	.	PUNCT
eurjchem-1150	130	1	the	the	DET
eurjchem-1150	130	2	reaction	reaction	NOUN
eurjchem-1150	130	3	mixture	mixture	NOUN
eurjchem-1150	130	4	was	be	AUX
eurjchem-1150	130	5	quenched	quench	VERB
eurjchem-1150	130	6	with	with	ADP
eurjchem-1150	130	7	aqueous	aqueous	ADJ
eurjchem-1150	130	8	nahco3	nahco3	NOUN
eurjchem-1150	130	9	solution	solution	NOUN
eurjchem-1150	130	10	(	(	PUNCT
eurjchem-1150	130	11	10	10	NUM
eurjchem-1150	130	12	%	%	NOUN
eurjchem-1150	130	13	,	,	PUNCT
eurjchem-1150	130	14	w	w	NOUN
eurjchem-1150	130	15	:	:	SYM
eurjchem-1150	130	16	v	v	NOUN
eurjchem-1150	130	17	,	,	PUNCT
eurjchem-1150	130	18	5	5	NUM
eurjchem-1150	130	19	ml	ml	NOUN
eurjchem-1150	130	20	)	)	PUNCT
eurjchem-1150	130	21	,	,	PUNCT
eurjchem-1150	130	22	and	and	CCONJ
eurjchem-1150	130	23	extracted	extract	VERB
eurjchem-1150	130	24	with	with	ADP
eurjchem-1150	130	25	etoac	etoac	ADJ
eurjchem-1150	130	26	.	.	PUNCT
eurjchem-1150	131	1	the	the	DET
eurjchem-1150	131	2	organic	organic	ADJ
eurjchem-1150	131	3	layer	layer	NOUN
eurjchem-1150	131	4	was	be	AUX
eurjchem-1150	131	5	dried	dry	VERB
eurjchem-1150	131	6	over	over	ADP
eurjchem-1150	131	7	anhydrous	anhydrous	ADJ
eurjchem-1150	131	8	mgso4	mgso4	NOUN
eurjchem-1150	131	9	,	,	PUNCT
eurjchem-1150	131	10	concentrated	concentrate	VERB
eurjchem-1150	131	11	under	under	ADP
eurjchem-1150	131	12	vacuum	vacuum	NOUN
eurjchem-1150	131	13	,	,	PUNCT
eurjchem-1150	131	14	and	and	CCONJ
eurjchem-1150	131	15	purified	purify	VERB
eurjchem-1150	131	16	by	by	ADP
eurjchem-1150	131	17	flash	flash	NOUN
eurjchem-1150	131	18	column	column	NOUN
eurjchem-1150	131	19	chromatography	chromatography	NOUN
eurjchem-1150	131	20	(	(	PUNCT
eurjchem-1150	131	21	hexane	hexane	NOUN
eurjchem-1150	131	22	:	:	PUNCT
eurjchem-1150	131	23	etoac	etoac	ADJ
eurjchem-1150	131	24	,	,	PUNCT
eurjchem-1150	131	25	9:1	9:1	NUM
eurjchem-1150	131	26	,	,	PUNCT
eurjchem-1150	131	27	v	v	NOUN
eurjchem-1150	131	28	:	:	SYM
eurjchem-1150	131	29	v	v	NOUN
eurjchem-1150	131	30	)	)	PUNCT
eurjchem-1150	131	31	to	to	PART
eurjchem-1150	131	32	afford	afford	VERB
eurjchem-1150	131	33	compound	compound	VERB
eurjchem-1150	131	34	13	13	NUM
eurjchem-1150	131	35	(	(	PUNCT
eurjchem-1150	131	36	scheme	scheme	NOUN
eurjchem-1150	131	37	1	1	NUM
eurjchem-1150	131	38	)	)	PUNCT
eurjchem-1150	131	39	.	.	PUNCT
eurjchem-1150	132	1	color	color	NOUN
eurjchem-1150	132	2	:	:	PUNCT
eurjchem-1150	132	3	colorless	colorless	ADJ
eurjchem-1150	132	4	oil	oil	NOUN
eurjchem-1150	132	5	.	.	PUNCT
eurjchem-1150	133	1	yield	yield	NOUN
eurjchem-1150	133	2	:	:	PUNCT
eurjchem-1150	133	3	0.54	0.54	NUM
eurjchem-1150	133	4	g	g	NOUN
eurjchem-1150	133	5	,	,	PUNCT
eurjchem-1150	133	6	99	99	NUM
eurjchem-1150	133	7	%	%	NOUN
eurjchem-1150	133	8	.	.	PUNCT
eurjchem-1150	134	1	ft‐ir	ft‐ir	NOUN
eurjchem-1150	134	2	(	(	PUNCT
eurjchem-1150	134	3	neat	neat	ADJ
eurjchem-1150	134	4	,	,	PUNCT
eurjchem-1150	134	5	ν	ν	NOUN
eurjchem-1150	134	6	,	,	PUNCT
eurjchem-1150	134	7	cm‐1	cm‐1	PROPN
eurjchem-1150	134	8	):	):	PUNCT
eurjchem-1150	134	9	2932	2932	NUM
eurjchem-1150	134	10	,	,	PUNCT
eurjchem-1150	134	11	1740	1740	NUM
eurjchem-1150	134	12	,	,	PUNCT
eurjchem-1150	134	13	1238	1238	NUM
eurjchem-1150	134	14	,	,	PUNCT
eurjchem-1150	134	15	1113	1113	NUM
eurjchem-1150	134	16	.	.	PUNCT
eurjchem-1150	135	1	1h	1h	NUM
eurjchem-1150	135	2	nmr	nmr	NOUN
eurjchem-1150	135	3	(	(	PUNCT
eurjchem-1150	135	4	300	300	NUM
eurjchem-1150	135	5	mhz	mhz	NOUN
eurjchem-1150	135	6	,	,	PUNCT
eurjchem-1150	135	7	cdcl3	cdcl3	PROPN
eurjchem-1150	135	8	,	,	PUNCT
eurjchem-1150	135	9	δ	δ	PROPN
eurjchem-1150	135	10	,	,	PUNCT
eurjchem-1150	135	11	ppm	ppm	NUM
eurjchem-1150	135	12	):	):	PUNCT
eurjchem-1150	135	13	0.87	0.87	NUM
eurjchem-1150	135	14	(	(	PUNCT
eurjchem-1150	135	15	t	t	PROPN
eurjchem-1150	135	16	,	,	PUNCT
eurjchem-1150	135	17	3h	3h	NUM
eurjchem-1150	135	18	,	,	PUNCT
eurjchem-1150	135	19	ch3‐ch2‐	ch3‐ch2‐	PROPN
eurjchem-1150	135	20	)	)	PUNCT
eurjchem-1150	135	21	,	,	PUNCT
eurjchem-1150	135	22	1.06	1.06	NUM
eurjchem-1150	135	23	(	(	PUNCT
eurjchem-1150	135	24	s	s	PROPN
eurjchem-1150	135	25	,	,	PUNCT
eurjchem-1150	135	26	9h	9h	NUM
eurjchem-1150	135	27	,	,	PUNCT
eurjchem-1150	135	28	(	(	PUNCT
eurjchem-1150	135	29	ch3)3c‐si	ch3)3c‐si	PROPN
eurjchem-1150	135	30	)	)	PUNCT
eurjchem-1150	135	31	,	,	PUNCT
eurjchem-1150	135	32	1.20‐1.34	1.20‐1.34	NUM
eurjchem-1150	135	33	(	(	PUNCT
eurjchem-1150	135	34	m	m	PROPN
eurjchem-1150	135	35	,	,	PUNCT
eurjchem-1150	135	36	4h	4h	NOUN
eurjchem-1150	135	37	,	,	PUNCT
eurjchem-1150	135	38	ch2‐ch2‐ch3	ch2‐ch2‐ch3	ADJ
eurjchem-1150	135	39	)	)	PUNCT
eurjchem-1150	135	40	,	,	PUNCT
eurjchem-1150	135	41	1.43	1.43	NUM
eurjchem-1150	135	42	(	(	PUNCT
eurjchem-1150	135	43	s	s	PROPN
eurjchem-1150	135	44	,	,	PUNCT
eurjchem-1150	135	45	6h	6h	NUM
eurjchem-1150	135	46	,	,	PUNCT
eurjchem-1150	135	47	(	(	PUNCT
eurjchem-1150	135	48	ch3)2c	ch3)2c	PROPN
eurjchem-1150	135	49	)	)	PUNCT
eurjchem-1150	135	50	,	,	PUNCT
eurjchem-1150	135	51	1.51‐1.65	1.51‐1.65	NUM
eurjchem-1150	135	52	(	(	PUNCT
eurjchem-1150	135	53	m	m	PROPN
eurjchem-1150	135	54	,	,	PUNCT
eurjchem-1150	135	55	2h	2h	NUM
eurjchem-1150	135	56	,	,	PUNCT
eurjchem-1150	135	57	ch2‐(ch2)2‐ch3	ch2‐(ch2)2‐ch3	ADJ
eurjchem-1150	135	58	)	)	PUNCT
eurjchem-1150	135	59	,	,	PUNCT
eurjchem-1150	135	60	2.05	2.05	NUM
eurjchem-1150	135	61	(	(	PUNCT
eurjchem-1150	135	62	s	s	PROPN
eurjchem-1150	135	63	,	,	PUNCT
eurjchem-1150	135	64	3h	3h	NUM
eurjchem-1150	135	65	,	,	PUNCT
eurjchem-1150	135	66	ch3‐co	ch3‐co	NOUN
eurjchem-1150	135	67	)	)	PUNCT
eurjchem-1150	135	68	,	,	PUNCT
eurjchem-1150	135	69	3.68‐3.84	3.68‐3.84	NUM
eurjchem-1150	135	70	(	(	PUNCT
eurjchem-1150	135	71	m	m	PROPN
eurjchem-1150	135	72	,	,	PUNCT
eurjchem-1150	135	73	3h	3h	NUM
eurjchem-1150	135	74	,	,	PUNCT
eurjchem-1150	135	75	ch2‐osi	ch2‐osi	PROPN
eurjchem-1150	135	76	,	,	PUNCT
eurjchem-1150	135	77	ch‐ch2‐osi	ch‐ch2‐osi	NOUN
eurjchem-1150	135	78	)	)	PUNCT
eurjchem-1150	135	79	,	,	PUNCT
eurjchem-1150	135	80	4.44‐4.50	4.44‐4.50	X
eurjchem-1150	135	81	(	(	PUNCT
eurjchem-1150	135	82	m	m	PROPN
eurjchem-1150	135	83	,	,	PUNCT
eurjchem-1150	135	84	1h	1h	NUM
eurjchem-1150	135	85	,	,	PUNCT
eurjchem-1150	135	86	hc‐ch=	hc‐ch=	PROPN
eurjchem-1150	135	87	)	)	PUNCT
eurjchem-1150	135	88	,	,	PUNCT
eurjchem-1150	135	89	5.21‐5.27	5.21‐5.27	NUM
eurjchem-1150	135	90	(	(	PUNCT
eurjchem-1150	135	91	m	m	PROPN
eurjchem-1150	135	92	,	,	PUNCT
eurjchem-1150	135	93	1h	1h	NUM
eurjchem-1150	135	94	,	,	PUNCT
eurjchem-1150	135	95	ch(oac	ch(oac	NOUN
eurjchem-1150	135	96	)	)	PUNCT
eurjchem-1150	135	97	)	)	PUNCT
eurjchem-1150	135	98	,	,	PUNCT
eurjchem-1150	135	99	5.68‐5.72	5.68‐5.72	NUM
eurjchem-1150	135	100	(	(	PUNCT
eurjchem-1150	135	101	m	m	PROPN
eurjchem-1150	135	102	,	,	PUNCT
eurjchem-1150	135	103	2h	2h	NUM
eurjchem-1150	135	104	,	,	PUNCT
eurjchem-1150	135	105	ch	ch	NOUN
eurjchem-1150	135	106	=	=	NOUN
eurjchem-1150	135	107	ch	ch	NOUN
eurjchem-1150	135	108	)	)	PUNCT
eurjchem-1150	135	109	,	,	PUNCT
eurjchem-1150	135	110	7.35‐7.43	7.35‐7.43	NUM
eurjchem-1150	135	111	(	(	PUNCT
eurjchem-1150	135	112	m	m	PROPN
eurjchem-1150	135	113	,	,	PUNCT
eurjchem-1150	135	114	6h	6h	NUM
eurjchem-1150	135	115	,	,	PUNCT
eurjchem-1150	135	116	ar‐h	ar‐h	PROPN
eurjchem-1150	135	117	)	)	PUNCT
eurjchem-1150	135	118	,	,	PUNCT
eurjchem-1150	135	119	7.65‐7.70	7.65‐7.70	NUM
eurjchem-1150	135	120	(	(	PUNCT
eurjchem-1150	135	121	m	m	PROPN
eurjchem-1150	135	122	,	,	PUNCT
eurjchem-1150	135	123	4h	4h	NOUN
eurjchem-1150	135	124	,	,	PUNCT
eurjchem-1150	135	125	ar‐h	ar‐h	PROPN
eurjchem-1150	135	126	)	)	PUNCT
eurjchem-1150	135	127	.	.	PUNCT
eurjchem-1150	136	1	13c	13c	NOUN
eurjchem-1150	136	2	nmr	nmr	NOUN
eurjchem-1150	136	3	(	(	PUNCT
eurjchem-1150	136	4	75	75	NUM
eurjchem-1150	136	5	mhz	mhz	NOUN
eurjchem-1150	136	6	,	,	PUNCT
eurjchem-1150	136	7	cdcl3	cdcl3	PROPN
eurjchem-1150	136	8	,	,	PUNCT
eurjchem-1150	136	9	δ	δ	PROPN
eurjchem-1150	136	10	,	,	PUNCT
eurjchem-1150	136	11	ppm	ppm	NUM
eurjchem-1150	136	12	):	):	PUNCT
eurjchem-1150	136	13	13.8	13.8	NUM
eurjchem-1150	136	14	,	,	PUNCT
eurjchem-1150	136	15	19.1	19.1	NUM
eurjchem-1150	136	16	,	,	PUNCT
eurjchem-1150	136	17	21.1	21.1	NUM
eurjchem-1150	136	18	,	,	PUNCT
eurjchem-1150	136	19	22.3	22.3	NUM
eurjchem-1150	136	20	,	,	PUNCT
eurjchem-1150	136	21	26.7	26.7	NUM
eurjchem-1150	136	22	,	,	PUNCT
eurjchem-1150	136	23	26.8	26.8	NUM
eurjchem-1150	136	24	,	,	PUNCT
eurjchem-1150	136	25	26.9	26.9	NUM
eurjchem-1150	136	26	,	,	PUNCT
eurjchem-1150	136	27	27.1	27.1	NUM
eurjchem-1150	136	28	,	,	PUNCT
eurjchem-1150	136	29	33.9	33.9	NUM
eurjchem-1150	136	30	,	,	PUNCT
eurjchem-1150	136	31	62.5	62.5	NUM
eurjchem-1150	136	32	,	,	PUNCT
eurjchem-1150	136	33	73.5	73.5	NUM
eurjchem-1150	136	34	,	,	PUNCT
eurjchem-1150	136	35	77.8	77.8	NUM
eurjchem-1150	136	36	,	,	PUNCT
eurjchem-1150	136	37	81.2	81.2	NUM
eurjchem-1150	136	38	,	,	PUNCT
eurjchem-1150	136	39	109	109	NUM
eurjchem-1150	136	40	,	,	PUNCT
eurjchem-1150	136	41	127.6	127.6	NUM
eurjchem-1150	136	42	,	,	PUNCT
eurjchem-1150	136	43	129.4	129.4	NUM
eurjchem-1150	136	44	,	,	PUNCT
eurjchem-1150	136	45	129.6	129.6	NUM
eurjchem-1150	136	46	,	,	PUNCT
eurjchem-1150	136	47	131.9	131.9	NUM
eurjchem-1150	136	48	,	,	PUNCT
eurjchem-1150	136	49	133.0	133.0	NUM
eurjchem-1150	136	50	,	,	PUNCT
eurjchem-1150	136	51	135.5	135.5	NUM
eurjchem-1150	136	52	,	,	PUNCT
eurjchem-1150	136	53	170	170	NUM
eurjchem-1150	136	54	.	.	PUNCT
eurjchem-1150	137	1	esi‐ms	esi‐ms	PROPN
eurjchem-1150	137	2	(	(	PUNCT
eurjchem-1150	137	3	m	m	PROPN
eurjchem-1150	137	4	/	/	SYM
eurjchem-1150	137	5	z	z	NOUN
eurjchem-1150	137	6	):	):	PUNCT
eurjchem-1150	137	7	547	547	NUM
eurjchem-1150	137	8	(	(	PUNCT
eurjchem-1150	137	9	m+na)+	m+na)+	NOUN
eurjchem-1150	137	10	.	.	PROPN
eurjchem-1150	137	11	hrms	hrm	VERB
eurjchem-1150	137	12	calcd	calcd	NOUN
eurjchem-1150	137	13	.	.	PUNCT
eurjchem-1150	138	1	for	for	ADP
eurjchem-1150	138	2	c31h44o5sina	c31h44o5sina	PRON
eurjchem-1150	138	3	[	[	X
eurjchem-1150	138	4	m+na]+	m+na]+	NOUN
eurjchem-1150	138	5	:	:	PUNCT
eurjchem-1150	138	6	547.2964	547.2964	NUM
eurjchem-1150	138	7	,	,	PUNCT
eurjchem-1150	138	8	found	find	VERB
eurjchem-1150	138	9	:	:	PUNCT
eurjchem-1150	138	10	547.2954	547.2954	NUM
eurjchem-1150	138	11	.	.	NOUN
eurjchem-1150	138	12	2.2.7	2.2.7	NUM
eurjchem-1150	138	13	.	.	PUNCT
eurjchem-1150	139	1	synthesis	synthesis	NOUN
eurjchem-1150	139	2	of	of	ADP
eurjchem-1150	139	3	(	(	PUNCT
eurjchem-1150	139	4	z)‐1‐((4s,5s)‐5‐(hydroxymethyl)‐2,2‐	z)‐1‐((4s,5s)‐5‐(hydroxymethyl)‐2,2‐	PROPN
eurjchem-1150	139	5	dimethyl‐1,3‐dioxolan‐4‐yl)hept‐1‐en‐3‐yl	dimethyl‐1,3‐dioxolan‐4‐yl)hept‐1‐en‐3‐yl	VERB
eurjchem-1150	139	6	acetate	acetate	NOUN
eurjchem-1150	139	7	(	(	PUNCT
eurjchem-1150	139	8	14	14	NUM
eurjchem-1150	139	9	)	)	PUNCT
eurjchem-1150	139	10	to	to	ADP
eurjchem-1150	139	11	a	a	DET
eurjchem-1150	139	12	stirred	stir	VERB
eurjchem-1150	139	13	solution	solution	NOUN
eurjchem-1150	139	14	of	of	ADP
eurjchem-1150	139	15	compound	compound	NOUN
eurjchem-1150	139	16	13	13	NUM
eurjchem-1150	139	17	(	(	PUNCT
eurjchem-1150	139	18	945	945	NUM
eurjchem-1150	139	19	mg	mg	PROPN
eurjchem-1150	139	20	,	,	PUNCT
eurjchem-1150	139	21	1.8	1.8	NUM
eurjchem-1150	139	22	mmol	mmol	NOUN
eurjchem-1150	139	23	)	)	PUNCT
eurjchem-1150	139	24	in	in	ADP
eurjchem-1150	139	25	dry	dry	ADJ
eurjchem-1150	139	26	thf	thf	NOUN
eurjchem-1150	139	27	(	(	PUNCT
eurjchem-1150	139	28	20	20	NUM
eurjchem-1150	139	29	ml	ml	NOUN
eurjchem-1150	139	30	)	)	PUNCT
eurjchem-1150	139	31	,	,	PUNCT
eurjchem-1150	139	32	tbaf	tbaf	INTJ
eurjchem-1150	139	33	(	(	PUNCT
eurjchem-1150	139	34	5.45	5.45	NUM
eurjchem-1150	139	35	ml	ml	NOUN
eurjchem-1150	139	36	,	,	PUNCT
eurjchem-1150	139	37	1	1	NUM
eurjchem-1150	139	38	m	m	NOUN
eurjchem-1150	139	39	in	in	ADP
eurjchem-1150	139	40	thf	thf	NOUN
eurjchem-1150	139	41	,	,	PUNCT
eurjchem-1150	139	42	5.41	5.41	NUM
eurjchem-1150	139	43	mmol	mmol	NOUN
eurjchem-1150	139	44	)	)	PUNCT
eurjchem-1150	139	45	was	be	AUX
eurjchem-1150	139	46	added	add	VERB
eurjchem-1150	139	47	at	at	ADP
eurjchem-1150	139	48	room	room	NOUN
eurjchem-1150	139	49	temperature	temperature	NOUN
eurjchem-1150	139	50	and	and	CCONJ
eurjchem-1150	139	51	the	the	DET
eurjchem-1150	139	52	resulting	result	VERB
eurjchem-1150	139	53	solution	solution	NOUN
eurjchem-1150	139	54	was	be	AUX
eurjchem-1150	139	55	stirred	stir	VERB
eurjchem-1150	139	56	for	for	ADP
eurjchem-1150	139	57	5	5	NUM
eurjchem-1150	139	58	h.	h.	NOUN
eurjchem-1150	139	59	the	the	DET
eurjchem-1150	139	60	solvent	solvent	NOUN
eurjchem-1150	139	61	was	be	AUX
eurjchem-1150	139	62	evaporated	evaporate	VERB
eurjchem-1150	139	63	under	under	ADP
eurjchem-1150	139	64	vacuum	vacuum	NOUN
eurjchem-1150	139	65	and	and	CCONJ
eurjchem-1150	139	66	purified	purify	VERB
eurjchem-1150	139	67	by	by	ADP
eurjchem-1150	139	68	flash	flash	NOUN
eurjchem-1150	139	69	column	column	NOUN
eurjchem-1150	139	70	chromatography	chromatography	NOUN
eurjchem-1150	139	71	(	(	PUNCT
eurjchem-1150	139	72	hexane	hexane	NOUN
eurjchem-1150	139	73	:	:	PUNCT
eurjchem-1150	139	74	etoac	etoac	ADJ
eurjchem-1150	139	75	,	,	PUNCT
eurjchem-1150	139	76	6:1	6:1	NUM
eurjchem-1150	139	77	,	,	PUNCT
eurjchem-1150	139	78	v	v	NOUN
eurjchem-1150	139	79	:	:	SYM
eurjchem-1150	139	80	v	v	NOUN
eurjchem-1150	139	81	)	)	PUNCT
eurjchem-1150	139	82	to	to	PART
eurjchem-1150	139	83	afford	afford	VERB
eurjchem-1150	139	84	compound	compound	VERB
eurjchem-1150	139	85	14	14	NUM
eurjchem-1150	139	86	(	(	PUNCT
eurjchem-1150	139	87	scheme	scheme	NOUN
eurjchem-1150	139	88	1	1	NUM
eurjchem-1150	139	89	)	)	PUNCT
eurjchem-1150	139	90	.	.	PUNCT
eurjchem-1150	140	1	color	color	NOUN
eurjchem-1150	140	2	:	:	PUNCT
eurjchem-1150	140	3	colorless	colorless	ADJ
eurjchem-1150	140	4	oil	oil	NOUN
eurjchem-1150	140	5	.	.	PUNCT
eurjchem-1150	141	1	yield	yield	NOUN
eurjchem-1150	141	2	:	:	PUNCT
eurjchem-1150	141	3	0.493	0.493	NUM
eurjchem-1150	141	4	g	g	NOUN
eurjchem-1150	141	5	,	,	PUNCT
eurjchem-1150	141	6	92	92	NUM
eurjchem-1150	141	7	%	%	NOUN
eurjchem-1150	141	8	.	.	PUNCT
eurjchem-1150	142	1	ft‐ir	ft‐ir	NOUN
eurjchem-1150	142	2	(	(	PUNCT
eurjchem-1150	142	3	neat	neat	ADJ
eurjchem-1150	142	4	,	,	PUNCT
eurjchem-1150	142	5	ν	ν	NOUN
eurjchem-1150	142	6	,	,	PUNCT
eurjchem-1150	142	7	cm‐1	cm‐1	PROPN
eurjchem-1150	142	8	):	):	PUNCT
eurjchem-1150	142	9	3451	3451	NUM
eurjchem-1150	142	10	,	,	PUNCT
eurjchem-1150	142	11	2934	2934	NUM
eurjchem-1150	142	12	,	,	PUNCT
eurjchem-1150	142	13	2873	2873	NUM
eurjchem-1150	142	14	,	,	PUNCT
eurjchem-1150	142	15	1738	1738	NUM
eurjchem-1150	142	16	,	,	PUNCT
eurjchem-1150	142	17	1240	1240	NUM
eurjchem-1150	142	18	,	,	PUNCT
eurjchem-1150	142	19	1048	1048	NUM
eurjchem-1150	142	20	.	.	PUNCT
eurjchem-1150	143	1	1h	1h	NUM
eurjchem-1150	143	2	nmr	nmr	NOUN
eurjchem-1150	143	3	(	(	PUNCT
eurjchem-1150	143	4	300	300	NUM
eurjchem-1150	143	5	mhz	mhz	NOUN
eurjchem-1150	143	6	,	,	PUNCT
eurjchem-1150	143	7	cdcl3	cdcl3	PROPN
eurjchem-1150	143	8	,	,	PUNCT
eurjchem-1150	143	9	δ	δ	PROPN
eurjchem-1150	143	10	,	,	PUNCT
eurjchem-1150	143	11	ppm	ppm	NOUN
eurjchem-1150	143	12	):	):	PUNCT
eurjchem-1150	143	13	0.89	0.89	NUM
eurjchem-1150	143	14	(	(	PUNCT
eurjchem-1150	143	15	t	t	PROPN
eurjchem-1150	143	16	,	,	PUNCT
eurjchem-1150	143	17	3h	3h	NUM
eurjchem-1150	143	18	,	,	PUNCT
eurjchem-1150	143	19	ch3‐ch2	ch3‐ch2	PROPN
eurjchem-1150	143	20	)	)	PUNCT
eurjchem-1150	143	21	,	,	PUNCT
eurjchem-1150	143	22	1.25‐1.36	1.25‐1.36	NUM
eurjchem-1150	143	23	(	(	PUNCT
eurjchem-1150	143	24	m	m	PROPN
eurjchem-1150	143	25	,	,	PUNCT
eurjchem-1150	143	26	4h	4h	NOUN
eurjchem-1150	143	27	,	,	PUNCT
eurjchem-1150	143	28	ch2‐ch2‐ch3	ch2‐ch2‐ch3	ADJ
eurjchem-1150	143	29	)	)	PUNCT
eurjchem-1150	143	30	,	,	PUNCT
eurjchem-1150	143	31	1.43	1.43	NUM
eurjchem-1150	143	32	(	(	PUNCT
eurjchem-1150	143	33	s	s	PROPN
eurjchem-1150	143	34	,	,	PUNCT
eurjchem-1150	143	35	6h	6h	NUM
eurjchem-1150	143	36	,	,	PUNCT
eurjchem-1150	143	37	(	(	PUNCT
eurjchem-1150	143	38	ch3)2c	ch3)2c	PROPN
eurjchem-1150	143	39	)	)	PUNCT
eurjchem-1150	143	40	,	,	PUNCT
eurjchem-1150	143	41	1.59‐1.63	1.59‐1.63	NUM
eurjchem-1150	143	42	(	(	PUNCT
eurjchem-1150	143	43	m	m	PROPN
eurjchem-1150	143	44	,	,	PUNCT
eurjchem-1150	143	45	2h	2h	NUM
eurjchem-1150	143	46	,	,	PUNCT
eurjchem-1150	143	47	ch2‐(ch2)2‐ch3	ch2‐(ch2)2‐ch3	ADJ
eurjchem-1150	143	48	)	)	PUNCT
eurjchem-1150	143	49	,	,	PUNCT
eurjchem-1150	143	50	2.04	2.04	NUM
eurjchem-1150	143	51	(	(	PUNCT
eurjchem-1150	143	52	s	s	PROPN
eurjchem-1150	143	53	,	,	PUNCT
eurjchem-1150	143	54	3h	3h	NUM
eurjchem-1150	143	55	,	,	PUNCT
eurjchem-1150	143	56	ch3‐	ch3‐	VERB
eurjchem-1150	143	57	co	co	NOUN
eurjchem-1150	143	58	)	)	PUNCT
eurjchem-1150	143	59	,	,	PUNCT
eurjchem-1150	143	60	3.55‐3.85	3.55‐3.85	NUM
eurjchem-1150	143	61	(	(	PUNCT
eurjchem-1150	143	62	m	m	PROPN
eurjchem-1150	143	63	,	,	PUNCT
eurjchem-1150	143	64	3h	3h	NUM
eurjchem-1150	143	65	,	,	PUNCT
eurjchem-1150	143	66	ch2‐oh	ch2‐oh	PROPN
eurjchem-1150	143	67	,	,	PUNCT
eurjchem-1150	143	68	ch‐ch2‐oh	ch‐ch2‐oh	NOUN
eurjchem-1150	143	69	)	)	PUNCT
eurjchem-1150	143	70	,	,	PUNCT
eurjchem-1150	143	71	4.32	4.32	NUM
eurjchem-1150	143	72	(	(	PUNCT
eurjchem-1150	143	73	m	m	PROPN
eurjchem-1150	143	74	,	,	PUNCT
eurjchem-1150	143	75	1h	1h	NUM
eurjchem-1150	143	76	,	,	PUNCT
eurjchem-1150	143	77	hc‐	hc‐	PROPN
eurjchem-1150	143	78	ch=	ch=	PROPN
eurjchem-1150	143	79	)	)	PUNCT
eurjchem-1150	143	80	,	,	PUNCT
eurjchem-1150	143	81	5.25	5.25	NUM
eurjchem-1150	143	82	(	(	PUNCT
eurjchem-1150	143	83	m	m	PROPN
eurjchem-1150	143	84	,	,	PUNCT
eurjchem-1150	143	85	1h	1h	NUM
eurjchem-1150	143	86	,	,	PUNCT
eurjchem-1150	143	87	ch(oac	ch(oac	NOUN
eurjchem-1150	143	88	)	)	PUNCT
eurjchem-1150	143	89	)	)	PUNCT
eurjchem-1150	143	90	,	,	PUNCT
eurjchem-1150	143	91	5.63‐5.83	5.63‐5.83	NUM
eurjchem-1150	143	92	(	(	PUNCT
eurjchem-1150	143	93	m	m	PROPN
eurjchem-1150	143	94	,	,	PUNCT
eurjchem-1150	143	95	2h	2h	NUM
eurjchem-1150	143	96	,	,	PUNCT
eurjchem-1150	143	97	ch	ch	NOUN
eurjchem-1150	143	98	=	=	NOUN
eurjchem-1150	143	99	ch	ch	NOUN
eurjchem-1150	143	100	)	)	PUNCT
eurjchem-1150	143	101	.	.	PUNCT
eurjchem-1150	144	1	13c	13c	NOUN
eurjchem-1150	144	2	96	96	NUM
eurjchem-1150	144	3	perla	perla	NOUN
eurjchem-1150	144	4	and	and	CCONJ
eurjchem-1150	144	5	fadnavis	fadnavis	NOUN
eurjchem-1150	144	6	/	/	SYM
eurjchem-1150	144	7	european	european	PROPN
eurjchem-1150	144	8	journal	journal	PROPN
eurjchem-1150	144	9	of	of	ADP
eurjchem-1150	144	10	chemistry	chemistry	NOUN
eurjchem-1150	144	11	6	6	NUM
eurjchem-1150	144	12	(	(	PUNCT
eurjchem-1150	144	13	1	1	NUM
eurjchem-1150	144	14	)	)	PUNCT
eurjchem-1150	144	15	(	(	PUNCT
eurjchem-1150	144	16	2015	2015	NUM
eurjchem-1150	144	17	)	)	PUNCT
eurjchem-1150	144	18	93‐97	93‐97	NUM
eurjchem-1150	144	19	nmr	nmr	NOUN
eurjchem-1150	144	20	(	(	PUNCT
eurjchem-1150	144	21	75	75	NUM
eurjchem-1150	144	22	mhz	mhz	NOUN
eurjchem-1150	144	23	,	,	PUNCT
eurjchem-1150	144	24	cdcl3	cdcl3	PROPN
eurjchem-1150	144	25	,	,	PUNCT
eurjchem-1150	144	26	δ	δ	PROPN
eurjchem-1150	144	27	,	,	PUNCT
eurjchem-1150	144	28	ppm	ppm	NUM
eurjchem-1150	144	29	):	):	PUNCT
eurjchem-1150	144	30	13.8	13.8	NUM
eurjchem-1150	144	31	,	,	PUNCT
eurjchem-1150	144	32	21.2	21.2	NUM
eurjchem-1150	144	33	,	,	PUNCT
eurjchem-1150	144	34	22.3	22.3	NUM
eurjchem-1150	144	35	,	,	PUNCT
eurjchem-1150	144	36	26.90	26.90	NUM
eurjchem-1150	144	37	,	,	PUNCT
eurjchem-1150	144	38	26.99	26.99	NUM
eurjchem-1150	144	39	,	,	PUNCT
eurjchem-1150	144	40	27.2	27.2	NUM
eurjchem-1150	144	41	,	,	PUNCT
eurjchem-1150	144	42	33.9	33.9	NUM
eurjchem-1150	144	43	,	,	PUNCT
eurjchem-1150	144	44	60.5	60.5	NUM
eurjchem-1150	144	45	,	,	PUNCT
eurjchem-1150	144	46	73.6	73.6	NUM
eurjchem-1150	144	47	,	,	PUNCT
eurjchem-1150	144	48	77.2	77.2	NUM
eurjchem-1150	144	49	,	,	PUNCT
eurjchem-1150	144	50	81.0	81.0	NUM
eurjchem-1150	144	51	,	,	PUNCT
eurjchem-1150	144	52	109.3	109.3	NUM
eurjchem-1150	144	53	,	,	PUNCT
eurjchem-1150	144	54	129.1	129.1	NUM
eurjchem-1150	144	55	,	,	PUNCT
eurjchem-1150	144	56	133.3	133.3	NUM
eurjchem-1150	144	57	,	,	PUNCT
eurjchem-1150	144	58	170.3	170.3	NUM
eurjchem-1150	144	59	.	.	PUNCT
eurjchem-1150	145	1	esi‐ms	esi‐ms	PROPN
eurjchem-1150	145	2	(	(	PUNCT
eurjchem-1150	145	3	m	m	PROPN
eurjchem-1150	145	4	/	/	SYM
eurjchem-1150	145	5	z	z	NOUN
eurjchem-1150	145	6	):	):	PUNCT
eurjchem-1150	145	7	287	287	NUM
eurjchem-1150	145	8	(	(	PUNCT
eurjchem-1150	145	9	m+1)+	m+1)+	NOUN
eurjchem-1150	145	10	,	,	PUNCT
eurjchem-1150	145	11	309	309	NUM
eurjchem-1150	145	12	(	(	PUNCT
eurjchem-1150	145	13	m+na)+	m+na)+	NOUN
eurjchem-1150	145	14	.	.	PROPN
eurjchem-1150	146	1	hrms	hrm	VERB
eurjchem-1150	146	2	calcd	calcd	NOUN
eurjchem-1150	146	3	.	.	PUNCT
eurjchem-1150	147	1	for	for	ADP
eurjchem-1150	147	2	c15h27o5	c15h27o5	PROPN
eurjchem-1150	147	3	[	[	X
eurjchem-1150	147	4	m+h]+	m+h]+	NOUN
eurjchem-1150	147	5	:	:	PUNCT
eurjchem-1150	147	6	287.1781	287.1781	NUM
eurjchem-1150	147	7	,	,	PUNCT
eurjchem-1150	147	8	found	find	VERB
eurjchem-1150	147	9	:	:	PUNCT
eurjchem-1150	147	10	287.1652	287.1652	NUM
eurjchem-1150	147	11	.	.	PUNCT
eurjchem-1150	148	1	2.2.8	2.2.8	NUM
eurjchem-1150	148	2	.	.	PUNCT
eurjchem-1150	149	1	synthesis	synthesis	NOUN
eurjchem-1150	149	2	of	of	ADP
eurjchem-1150	149	3	(	(	PUNCT
eurjchem-1150	149	4	z)‐ethyl	z)‐ethyl	PROPN
eurjchem-1150	149	5	3‐((4s,5s)‐5‐((z)‐3‐acetoxyhept‐	3‐((4s,5s)‐5‐((z)‐3‐acetoxyhept‐	NUM
eurjchem-1150	149	6	1‐enyl)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)acrylate	1‐enyl)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)acrylate	NOUN
eurjchem-1150	149	7	(	(	PUNCT
eurjchem-1150	149	8	15	15	NUM
eurjchem-1150	149	9	)	)	PUNCT
eurjchem-1150	149	10	to	to	ADP
eurjchem-1150	149	11	a	a	DET
eurjchem-1150	149	12	stirred	stir	VERB
eurjchem-1150	149	13	solution	solution	NOUN
eurjchem-1150	149	14	of	of	ADP
eurjchem-1150	149	15	(	(	PUNCT
eurjchem-1150	149	16	cocl)2	cocl)2	X
eurjchem-1150	149	17	(	(	PUNCT
eurjchem-1150	149	18	0.25	0.25	NUM
eurjchem-1150	149	19	ml	ml	NOUN
eurjchem-1150	149	20	,	,	PUNCT
eurjchem-1150	149	21	2.8	2.8	NUM
eurjchem-1150	149	22	mmol	mmol	NOUN
eurjchem-1150	149	23	)	)	PUNCT
eurjchem-1150	149	24	in	in	ADP
eurjchem-1150	149	25	dry	dry	ADJ
eurjchem-1150	149	26	ch2cl2	ch2cl2	PUNCT
eurjchem-1150	149	27	(	(	PUNCT
eurjchem-1150	149	28	30	30	NUM
eurjchem-1150	149	29	ml	ml	NOUN
eurjchem-1150	149	30	)	)	PUNCT
eurjchem-1150	149	31	was	be	AUX
eurjchem-1150	149	32	added	add	VERB
eurjchem-1150	149	33	anhydrous	anhydrous	ADJ
eurjchem-1150	149	34	dmso	dmso	NOUN
eurjchem-1150	149	35	(	(	PUNCT
eurjchem-1150	149	36	0.4	0.4	NUM
eurjchem-1150	149	37	ml	ml	NOUN
eurjchem-1150	149	38	,	,	PUNCT
eurjchem-1150	149	39	5.6	5.6	NUM
eurjchem-1150	149	40	mmol	mmol	NOUN
eurjchem-1150	149	41	)	)	PUNCT
eurjchem-1150	149	42	at	at	ADP
eurjchem-1150	149	43	‐78	‐78	NOUN
eurjchem-1150	149	44	°	°	ADP
eurjchem-1150	149	45	c	c	NOUN
eurjchem-1150	149	46	over	over	ADP
eurjchem-1150	149	47	a	a	DET
eurjchem-1150	149	48	period	period	NOUN
eurjchem-1150	149	49	of	of	ADP
eurjchem-1150	149	50	20	20	NUM
eurjchem-1150	149	51	min	min	NOUN
eurjchem-1150	149	52	under	under	ADP
eurjchem-1150	149	53	nitrogen	nitrogen	NOUN
eurjchem-1150	149	54	atmosphere	atmosphere	NOUN
eurjchem-1150	149	55	,	,	PUNCT
eurjchem-1150	149	56	and	and	CCONJ
eurjchem-1150	149	57	the	the	DET
eurjchem-1150	149	58	reaction	reaction	NOUN
eurjchem-1150	149	59	mixture	mixture	NOUN
eurjchem-1150	149	60	was	be	AUX
eurjchem-1150	149	61	stirred	stir	VERB
eurjchem-1150	149	62	for	for	ADP
eurjchem-1150	149	63	30	30	NUM
eurjchem-1150	149	64	min	min	NOUN
eurjchem-1150	149	65	.	.	PUNCT
eurjchem-1150	150	1	a	a	DET
eurjchem-1150	150	2	solution	solution	NOUN
eurjchem-1150	150	3	of	of	ADP
eurjchem-1150	150	4	compound	compound	NOUN
eurjchem-1150	150	5	14	14	NUM
eurjchem-1150	150	6	(	(	PUNCT
eurjchem-1150	150	7	400	400	NUM
eurjchem-1150	150	8	mg	mg	PROPN
eurjchem-1150	150	9	,	,	PUNCT
eurjchem-1150	150	10	1.4	1.4	NUM
eurjchem-1150	150	11	mmol	mmol	NOUN
eurjchem-1150	150	12	.	.	PUNCT
eurjchem-1150	150	13	)	)	PUNCT
eurjchem-1150	151	1	in	in	ADP
eurjchem-1150	151	2	ch2cl2	ch2cl2	PUNCT
eurjchem-1150	151	3	was	be	AUX
eurjchem-1150	151	4	added	add	VERB
eurjchem-1150	151	5	and	and	CCONJ
eurjchem-1150	151	6	the	the	DET
eurjchem-1150	151	7	resulting	result	VERB
eurjchem-1150	151	8	solution	solution	NOUN
eurjchem-1150	151	9	was	be	AUX
eurjchem-1150	151	10	stirred	stir	VERB
eurjchem-1150	151	11	for	for	ADP
eurjchem-1150	151	12	1	1	NUM
eurjchem-1150	151	13	h	h	NOUN
eurjchem-1150	151	14	at	at	ADP
eurjchem-1150	151	15	‐78	‐78	NOUN
eurjchem-1150	151	16	°	°	ADP
eurjchem-1150	151	17	c	c	NOUN
eurjchem-1150	151	18	.	.	PUNCT
eurjchem-1150	152	1	the	the	DET
eurjchem-1150	152	2	reaction	reaction	NOUN
eurjchem-1150	152	3	was	be	AUX
eurjchem-1150	152	4	quenched	quench	VERB
eurjchem-1150	152	5	with	with	ADP
eurjchem-1150	152	6	et3n	et3n	PROPN
eurjchem-1150	152	7	(	(	PUNCT
eurjchem-1150	152	8	1.17	1.17	NUM
eurjchem-1150	152	9	ml	ml	NOUN
eurjchem-1150	152	10	,	,	PUNCT
eurjchem-1150	152	11	8.4	8.4	NUM
eurjchem-1150	152	12	mmol	mmol	NOUN
eurjchem-1150	152	13	)	)	PUNCT
eurjchem-1150	152	14	,	,	PUNCT
eurjchem-1150	152	15	allowed	allow	VERB
eurjchem-1150	152	16	to	to	PART
eurjchem-1150	152	17	reach	reach	VERB
eurjchem-1150	152	18	room	room	NOUN
eurjchem-1150	152	19	temperature	temperature	NOUN
eurjchem-1150	152	20	and	and	CCONJ
eurjchem-1150	152	21	then	then	ADV
eurjchem-1150	152	22	extracted	extract	VERB
eurjchem-1150	152	23	with	with	ADP
eurjchem-1150	152	24	ch2cl2	ch2cl2	NOUN
eurjchem-1150	152	25	.	.	PUNCT
eurjchem-1150	153	1	the	the	DET
eurjchem-1150	153	2	combined	combine	VERB
eurjchem-1150	153	3	organic	organic	ADJ
eurjchem-1150	153	4	layer	layer	NOUN
eurjchem-1150	153	5	was	be	AUX
eurjchem-1150	153	6	dried	dry	VERB
eurjchem-1150	153	7	over	over	ADP
eurjchem-1150	153	8	anhydrous	anhydrous	ADJ
eurjchem-1150	153	9	mgso4	mgso4	NOUN
eurjchem-1150	153	10	and	and	CCONJ
eurjchem-1150	153	11	evaporated	evaporate	VERB
eurjchem-1150	153	12	under	under	ADP
eurjchem-1150	153	13	vacuum	vacuum	NOUN
eurjchem-1150	153	14	to	to	PART
eurjchem-1150	153	15	obtain	obtain	VERB
eurjchem-1150	153	16	crude	crude	ADJ
eurjchem-1150	153	17	aldehyde	aldehyde	NOUN
eurjchem-1150	153	18	which	which	PRON
eurjchem-1150	153	19	was	be	AUX
eurjchem-1150	153	20	employed	employ	VERB
eurjchem-1150	153	21	to	to	ADP
eurjchem-1150	153	22	the	the	DET
eurjchem-1150	153	23	next	next	ADJ
eurjchem-1150	153	24	step	step	NOUN
eurjchem-1150	153	25	immediately	immediately	ADV
eurjchem-1150	153	26	.	.	PUNCT
eurjchem-1150	154	1	to	to	ADP
eurjchem-1150	154	2	a	a	DET
eurjchem-1150	154	3	stirred	stir	VERB
eurjchem-1150	154	4	solution	solution	NOUN
eurjchem-1150	154	5	of	of	ADP
eurjchem-1150	154	6	(	(	PUNCT
eurjchem-1150	154	7	f3cch2o)2poch2cooet	f3cch2o)2poch2cooet	VERB
eurjchem-1150	154	8	(	(	PUNCT
eurjchem-1150	154	9	0.354	0.354	NUM
eurjchem-1150	154	10	ml	ml	NOUN
eurjchem-1150	154	11	,	,	PUNCT
eurjchem-1150	154	12	1.67	1.67	NUM
eurjchem-1150	154	13	mmol	mmol	NOUN
eurjchem-1150	154	14	)	)	PUNCT
eurjchem-1150	154	15	,	,	PUNCT
eurjchem-1150	154	16	18‐crown‐6	18‐crown‐6	NUM
eurjchem-1150	154	17	(	(	PUNCT
eurjchem-1150	154	18	1.478	1.478	NUM
eurjchem-1150	154	19	g	g	NOUN
eurjchem-1150	154	20	,	,	PUNCT
eurjchem-1150	154	21	5.6	5.6	NUM
eurjchem-1150	154	22	mmol	mmol	NOUN
eurjchem-1150	154	23	)	)	PUNCT
eurjchem-1150	154	24	in	in	ADP
eurjchem-1150	154	25	dry	dry	ADJ
eurjchem-1150	154	26	thf	thf	NOUN
eurjchem-1150	154	27	(	(	PUNCT
eurjchem-1150	154	28	2	2	NUM
eurjchem-1150	154	29	ml	ml	NOUN
eurjchem-1150	154	30	)	)	PUNCT
eurjchem-1150	154	31	at	at	ADP
eurjchem-1150	154	32	‐78	‐78	NOUN
eurjchem-1150	154	33	°	°	ADP
eurjchem-1150	154	34	c	c	PROPN
eurjchem-1150	154	35	was	be	AUX
eurjchem-1150	154	36	added	add	VERB
eurjchem-1150	154	37	khmds	khmds	NOUN
eurjchem-1150	154	38	(	(	PUNCT
eurjchem-1150	154	39	0.362	0.362	NUM
eurjchem-1150	154	40	g	g	NOUN
eurjchem-1150	154	41	,	,	PUNCT
eurjchem-1150	154	42	1081	1081	NUM
eurjchem-1150	154	43	mmol	mmol	NOUN
eurjchem-1150	154	44	)	)	PUNCT
eurjchem-1150	154	45	and	and	CCONJ
eurjchem-1150	154	46	stirred	stir	VERB
eurjchem-1150	154	47	for	for	ADP
eurjchem-1150	154	48	30	30	NUM
eurjchem-1150	154	49	min	min	NOUN
eurjchem-1150	154	50	.	.	PUNCT
eurjchem-1150	155	1	the	the	DET
eurjchem-1150	155	2	solution	solution	NOUN
eurjchem-1150	155	3	of	of	ADP
eurjchem-1150	155	4	crude	crude	ADJ
eurjchem-1150	155	5	aldehyde	aldehyde	NOUN
eurjchem-1150	155	6	in	in	ADP
eurjchem-1150	155	7	thf	thf	NOUN
eurjchem-1150	155	8	(	(	PUNCT
eurjchem-1150	155	9	5	5	NUM
eurjchem-1150	155	10	ml	ml	NOUN
eurjchem-1150	155	11	)	)	PUNCT
eurjchem-1150	155	12	was	be	AUX
eurjchem-1150	155	13	added	add	VERB
eurjchem-1150	155	14	,	,	PUNCT
eurjchem-1150	155	15	reaction	reaction	NOUN
eurjchem-1150	155	16	mixture	mixture	NOUN
eurjchem-1150	155	17	was	be	AUX
eurjchem-1150	155	18	stirred	stir	VERB
eurjchem-1150	155	19	for	for	ADP
eurjchem-1150	155	20	4	4	NUM
eurjchem-1150	155	21	h	h	NOUN
eurjchem-1150	155	22	at	at	ADP
eurjchem-1150	155	23	same	same	ADJ
eurjchem-1150	155	24	temperature	temperature	NOUN
eurjchem-1150	155	25	.	.	PUNCT
eurjchem-1150	156	1	the	the	DET
eurjchem-1150	156	2	reaction	reaction	NOUN
eurjchem-1150	156	3	was	be	AUX
eurjchem-1150	156	4	quenched	quench	VERB
eurjchem-1150	156	5	with	with	ADP
eurjchem-1150	156	6	saturated	saturate	VERB
eurjchem-1150	156	7	aqueous	aqueous	ADJ
eurjchem-1150	156	8	nh4cl	nh4cl	NOUN
eurjchem-1150	156	9	(	(	PUNCT
eurjchem-1150	156	10	5	5	NUM
eurjchem-1150	156	11	ml	ml	NOUN
eurjchem-1150	156	12	)	)	PUNCT
eurjchem-1150	156	13	and	and	CCONJ
eurjchem-1150	156	14	extracted	extract	VERB
eurjchem-1150	156	15	with	with	ADP
eurjchem-1150	156	16	ethyl	ethyl	PROPN
eurjchem-1150	156	17	acetate	acetate	NOUN
eurjchem-1150	156	18	.	.	PUNCT
eurjchem-1150	157	1	the	the	DET
eurjchem-1150	157	2	combined	combine	VERB
eurjchem-1150	157	3	organic	organic	ADJ
eurjchem-1150	157	4	layers	layer	NOUN
eurjchem-1150	157	5	were	be	AUX
eurjchem-1150	157	6	dried	dry	VERB
eurjchem-1150	157	7	over	over	ADP
eurjchem-1150	157	8	anhydrous	anhydrous	ADJ
eurjchem-1150	157	9	mgso4	mgso4	NOUN
eurjchem-1150	157	10	,	,	PUNCT
eurjchem-1150	157	11	concentrated	concentrate	VERB
eurjchem-1150	157	12	under	under	ADP
eurjchem-1150	157	13	vacuum	vacuum	NOUN
eurjchem-1150	157	14	,	,	PUNCT
eurjchem-1150	157	15	and	and	CCONJ
eurjchem-1150	157	16	the	the	DET
eurjchem-1150	157	17	residue	residue	NOUN
eurjchem-1150	157	18	was	be	AUX
eurjchem-1150	157	19	purified	purify	VERB
eurjchem-1150	157	20	by	by	ADP
eurjchem-1150	157	21	flash	flash	NOUN
eurjchem-1150	157	22	column	column	NOUN
eurjchem-1150	157	23	chromatography	chromatography	NOUN
eurjchem-1150	157	24	(	(	PUNCT
eurjchem-1150	157	25	hexane	hexane	NOUN
eurjchem-1150	157	26	:	:	PUNCT
eurjchem-1150	157	27	etoac	etoac	ADJ
eurjchem-1150	157	28	,	,	PUNCT
eurjchem-1150	157	29	8:2	8:2	NUM
eurjchem-1150	157	30	,	,	PUNCT
eurjchem-1150	157	31	v	v	NOUN
eurjchem-1150	157	32	:	:	SYM
eurjchem-1150	157	33	v	v	NOUN
eurjchem-1150	157	34	)	)	PUNCT
eurjchem-1150	157	35	to	to	PART
eurjchem-1150	157	36	afford	afford	VERB
eurjchem-1150	157	37	compound	compound	VERB
eurjchem-1150	157	38	15	15	NUM
eurjchem-1150	157	39	(	(	PUNCT
eurjchem-1150	157	40	scheme	scheme	NOUN
eurjchem-1150	157	41	1	1	NUM
eurjchem-1150	157	42	)	)	PUNCT
eurjchem-1150	157	43	.	.	PUNCT
eurjchem-1150	158	1	color	color	NOUN
eurjchem-1150	158	2	:	:	PUNCT
eurjchem-1150	158	3	colorless	colorless	ADJ
eurjchem-1150	158	4	oil	oil	NOUN
eurjchem-1150	158	5	.	.	PUNCT
eurjchem-1150	159	1	yield	yield	NOUN
eurjchem-1150	159	2	:	:	PUNCT
eurjchem-1150	159	3	0.396	0.396	NUM
eurjchem-1150	159	4	g	g	NOUN
eurjchem-1150	159	5	,	,	PUNCT
eurjchem-1150	159	6	80	80	NUM
eurjchem-1150	159	7	%	%	NOUN
eurjchem-1150	159	8	.	.	PUNCT
eurjchem-1150	160	1	ft‐ir	ft‐ir	NOUN
eurjchem-1150	160	2	(	(	PUNCT
eurjchem-1150	160	3	neat	neat	ADJ
eurjchem-1150	160	4	,	,	PUNCT
eurjchem-1150	160	5	ν	ν	NOUN
eurjchem-1150	160	6	,	,	PUNCT
eurjchem-1150	160	7	cm‐1	cm‐1	PROPN
eurjchem-1150	160	8	):	):	PUNCT
eurjchem-1150	160	9	2937	2937	NUM
eurjchem-1150	160	10	,	,	PUNCT
eurjchem-1150	160	11	1725	1725	NUM
eurjchem-1150	160	12	,	,	PUNCT
eurjchem-1150	160	13	1371	1371	NUM
eurjchem-1150	160	14	,	,	PUNCT
eurjchem-1150	160	15	1234	1234	NUM
eurjchem-1150	160	16	,	,	PUNCT
eurjchem-1150	160	17	1048	1048	NUM
eurjchem-1150	160	18	.	.	PUNCT
eurjchem-1150	161	1	1h	1h	NUM
eurjchem-1150	161	2	nmr	nmr	NOUN
eurjchem-1150	161	3	(	(	PUNCT
eurjchem-1150	161	4	300	300	NUM
eurjchem-1150	161	5	mhz	mhz	NOUN
eurjchem-1150	161	6	,	,	PUNCT
eurjchem-1150	161	7	cdcl3	cdcl3	PROPN
eurjchem-1150	161	8	,	,	PUNCT
eurjchem-1150	161	9	δ	δ	PROPN
eurjchem-1150	161	10	,	,	PUNCT
eurjchem-1150	161	11	ppm	ppm	NUM
eurjchem-1150	161	12	):	):	PUNCT
eurjchem-1150	161	13	0.88	0.88	NUM
eurjchem-1150	161	14	(	(	PUNCT
eurjchem-1150	161	15	t	t	PROPN
eurjchem-1150	161	16	,	,	PUNCT
eurjchem-1150	161	17	3h	3h	NUM
eurjchem-1150	161	18	,	,	PUNCT
eurjchem-1150	161	19	ch3‐	ch3‐	NOUN
eurjchem-1150	161	20	(	(	PUNCT
eurjchem-1150	161	21	ch2)2	ch2)2	NOUN
eurjchem-1150	161	22	)	)	PUNCT
eurjchem-1150	161	23	,	,	PUNCT
eurjchem-1150	161	24	1.25‐1.31	1.25‐1.31	NUM
eurjchem-1150	161	25	(	(	PUNCT
eurjchem-1150	161	26	m	m	PROPN
eurjchem-1150	161	27	,	,	PUNCT
eurjchem-1150	161	28	7h	7h	PROPN
eurjchem-1150	161	29	,	,	PUNCT
eurjchem-1150	161	30	(	(	PUNCT
eurjchem-1150	161	31	(	(	PUNCT
eurjchem-1150	161	32	ch2)2‐ch3	ch2)2‐ch3	NUM
eurjchem-1150	161	33	,	,	PUNCT
eurjchem-1150	161	34	ch3‐ch2‐o	ch3‐ch2‐o	NOUN
eurjchem-1150	161	35	)	)	PUNCT
eurjchem-1150	161	36	,	,	PUNCT
eurjchem-1150	161	37	1.45	1.45	NUM
eurjchem-1150	161	38	(	(	PUNCT
eurjchem-1150	161	39	s	s	PROPN
eurjchem-1150	161	40	,	,	PUNCT
eurjchem-1150	161	41	6h	6h	NUM
eurjchem-1150	161	42	,	,	PUNCT
eurjchem-1150	161	43	(	(	PUNCT
eurjchem-1150	161	44	ch3)2c	ch3)2c	PROPN
eurjchem-1150	161	45	)	)	PUNCT
eurjchem-1150	161	46	,	,	PUNCT
eurjchem-1150	161	47	1.53‐1.66	1.53‐1.66	NUM
eurjchem-1150	161	48	(	(	PUNCT
eurjchem-1150	161	49	m	m	PROPN
eurjchem-1150	161	50	,	,	PUNCT
eurjchem-1150	161	51	2h	2h	NUM
eurjchem-1150	161	52	,	,	PUNCT
eurjchem-1150	161	53	ch2‐(ch2)2‐ch3	ch2‐(ch2)2‐ch3	ADJ
eurjchem-1150	161	54	)	)	PUNCT
eurjchem-1150	161	55	,	,	PUNCT
eurjchem-1150	161	56	2.0	2.0	NUM
eurjchem-1150	161	57	(	(	PUNCT
eurjchem-1150	161	58	s	s	PROPN
eurjchem-1150	161	59	,	,	PUNCT
eurjchem-1150	161	60	3h	3h	NUM
eurjchem-1150	161	61	,	,	PUNCT
eurjchem-1150	161	62	ch3‐	ch3‐	VERB
eurjchem-1150	161	63	co	co	NOUN
eurjchem-1150	161	64	)	)	PUNCT
eurjchem-1150	161	65	,	,	PUNCT
eurjchem-1150	161	66	4.03‐4.22	4.03‐4.22	NUM
eurjchem-1150	161	67	(	(	PUNCT
eurjchem-1150	161	68	m	m	PROPN
eurjchem-1150	161	69	,	,	PUNCT
eurjchem-1150	161	70	3h	3h	NUM
eurjchem-1150	161	71	,	,	PUNCT
eurjchem-1150	161	72	o‐ch2‐ch3	o‐ch2‐ch3	ADJ
eurjchem-1150	161	73	,	,	PUNCT
eurjchem-1150	161	74	ch‐ch	ch‐ch	NOUN
eurjchem-1150	161	75	=	=	NOUN
eurjchem-1150	161	76	ch	ch	NOUN
eurjchem-1150	161	77	)	)	PUNCT
eurjchem-1150	161	78	,	,	PUNCT
eurjchem-1150	161	79	5.22‐5.30	5.22‐5.30	NUM
eurjchem-1150	161	80	(	(	PUNCT
eurjchem-1150	161	81	m	m	PROPN
eurjchem-1150	161	82	,	,	PUNCT
eurjchem-1150	161	83	1h	1h	NUM
eurjchem-1150	161	84	,	,	PUNCT
eurjchem-1150	161	85	ch‐ch	ch‐ch	NOUN
eurjchem-1150	161	86	=	=	NOUN
eurjchem-1150	161	87	ch‐coo	ch‐coo	NOUN
eurjchem-1150	161	88	)	)	PUNCT
eurjchem-1150	161	89	,	,	PUNCT
eurjchem-1150	161	90	5.38‐5.46	5.38‐5.46	NUM
eurjchem-1150	161	91	(	(	PUNCT
eurjchem-1150	161	92	m	m	PROPN
eurjchem-1150	161	93	,	,	PUNCT
eurjchem-1150	161	94	1h	1h	NUM
eurjchem-1150	161	95	,	,	PUNCT
eurjchem-1150	161	96	ch(oac	ch(oac	NOUN
eurjchem-1150	161	97	)	)	PUNCT
eurjchem-1150	161	98	)	)	PUNCT
eurjchem-1150	161	99	,	,	PUNCT
eurjchem-1150	161	100	5.71‐5.76	5.71‐5.76	NUM
eurjchem-1150	161	101	(	(	PUNCT
eurjchem-1150	161	102	m	m	PROPN
eurjchem-1150	161	103	,	,	PUNCT
eurjchem-1150	161	104	2h	2h	NUM
eurjchem-1150	161	105	,	,	PUNCT
eurjchem-1150	161	106	ch	ch	NOUN
eurjchem-1150	161	107	=	=	NOUN
eurjchem-1150	161	108	ch‐ch(oac	ch‐ch(oac	X
eurjchem-1150	161	109	)	)	PUNCT
eurjchem-1150	161	110	)	)	PUNCT
eurjchem-1150	161	111	,	,	PUNCT
eurjchem-1150	161	112	5.93	5.93	NUM
eurjchem-1150	161	113	(	(	PUNCT
eurjchem-1150	161	114	d	d	PROPN
eurjchem-1150	161	115	,	,	PUNCT
eurjchem-1150	161	116	1h	1h	NUM
eurjchem-1150	161	117	,	,	PUNCT
eurjchem-1150	161	118	j	j	PROPN
eurjchem-1150	161	119	=	=	PROPN
eurjchem-1150	161	120	11.3	11.3	NUM
eurjchem-1150	161	121	hz	hz	VERB
eurjchem-1150	161	122	,	,	PUNCT
eurjchem-1150	161	123	ch‐cooet	ch‐cooet	ADJ
eurjchem-1150	161	124	)	)	PUNCT
eurjchem-1150	161	125	,	,	PUNCT
eurjchem-1150	161	126	6.12	6.12	NUM
eurjchem-1150	161	127	(	(	PUNCT
eurjchem-1150	161	128	dd	dd	PROPN
eurjchem-1150	161	129	,	,	PUNCT
eurjchem-1150	161	130	1h	1h	NUM
eurjchem-1150	161	131	,	,	PUNCT
eurjchem-1150	161	132	j	j	PROPN
eurjchem-1150	161	133	=	=	SYM
eurjchem-1150	161	134	8.3	8.3	NUM
eurjchem-1150	161	135	,	,	PUNCT
eurjchem-1150	161	136	3.0	3.0	NUM
eurjchem-1150	161	137	hz	hz	NOUN
eurjchem-1150	161	138	,	,	PUNCT
eurjchem-1150	161	139	hc	hc	PROPN
eurjchem-1150	161	140	=	=	NOUN
eurjchem-1150	161	141	ch‐cooet	ch‐cooet	ADJ
eurjchem-1150	161	142	)	)	PUNCT
eurjchem-1150	161	143	.	.	PUNCT
eurjchem-1150	162	1	13c	13c	NOUN
eurjchem-1150	162	2	nmr	nmr	NOUN
eurjchem-1150	162	3	(	(	PUNCT
eurjchem-1150	162	4	75	75	NUM
eurjchem-1150	162	5	mhz	mhz	NOUN
eurjchem-1150	162	6	,	,	PUNCT
eurjchem-1150	162	7	cdcl3	cdcl3	PROPN
eurjchem-1150	162	8	,	,	PUNCT
eurjchem-1150	162	9	δ	δ	PROPN
eurjchem-1150	162	10	,	,	PUNCT
eurjchem-1150	162	11	ppm	ppm	NUM
eurjchem-1150	162	12	):	):	PUNCT
eurjchem-1150	162	13	13.8	13.8	NUM
eurjchem-1150	162	14	,	,	PUNCT
eurjchem-1150	162	15	14.0	14.0	NUM
eurjchem-1150	162	16	,	,	PUNCT
eurjchem-1150	162	17	21.1	21.1	NUM
eurjchem-1150	162	18	,	,	PUNCT
eurjchem-1150	162	19	22.3	22.3	NUM
eurjchem-1150	162	20	,	,	PUNCT
eurjchem-1150	162	21	26.9	26.9	NUM
eurjchem-1150	162	22	,	,	PUNCT
eurjchem-1150	162	23	27.01	27.01	NUM
eurjchem-1150	162	24	,	,	PUNCT
eurjchem-1150	162	25	27.06	27.06	NUM
eurjchem-1150	162	26	,	,	PUNCT
eurjchem-1150	162	27	33.8	33.8	NUM
eurjchem-1150	162	28	,	,	PUNCT
eurjchem-1150	162	29	60.2	60.2	NUM
eurjchem-1150	162	30	,	,	PUNCT
eurjchem-1150	162	31	73.2	73.2	NUM
eurjchem-1150	162	32	,	,	PUNCT
eurjchem-1150	162	33	75.8	75.8	NUM
eurjchem-1150	162	34	,	,	PUNCT
eurjchem-1150	162	35	81.4	81.4	NUM
eurjchem-1150	162	36	,	,	PUNCT
eurjchem-1150	162	37	109.8	109.8	NUM
eurjchem-1150	162	38	,	,	PUNCT
eurjchem-1150	162	39	123.3	123.3	NUM
eurjchem-1150	162	40	,	,	PUNCT
eurjchem-1150	162	41	127.9	127.9	NUM
eurjchem-1150	162	42	,	,	PUNCT
eurjchem-1150	162	43	133.2	133.2	NUM
eurjchem-1150	162	44	,	,	PUNCT
eurjchem-1150	162	45	143.8	143.8	NUM
eurjchem-1150	162	46	,	,	PUNCT
eurjchem-1150	162	47	164.9	164.9	NUM
eurjchem-1150	162	48	,	,	PUNCT
eurjchem-1150	162	49	170.0	170.0	NUM
eurjchem-1150	162	50	.	.	PUNCT
eurjchem-1150	163	1	esi‐ms	esi‐ms	PROPN
eurjchem-1150	163	2	(	(	PUNCT
eurjchem-1150	163	3	m	m	PROPN
eurjchem-1150	163	4	/	/	SYM
eurjchem-1150	163	5	z	z	NOUN
eurjchem-1150	163	6	):	):	PUNCT
eurjchem-1150	163	7	377	377	NUM
eurjchem-1150	163	8	(	(	PUNCT
eurjchem-1150	163	9	m+na)+	m+na)+	NOUN
eurjchem-1150	163	10	.	.	PROPN
eurjchem-1150	163	11	hrms	hrm	VERB
eurjchem-1150	163	12	calcd	calcd	NOUN
eurjchem-1150	163	13	.	.	PUNCT
eurjchem-1150	164	1	for	for	ADP
eurjchem-1150	164	2	c19h30o6na	c19h30o6na	NOUN
eurjchem-1150	165	1	[	[	X
eurjchem-1150	165	2	m+na]+	m+na]+	NOUN
eurjchem-1150	165	3	:	:	PUNCT
eurjchem-1150	165	4	377.2042	377.2042	NUM
eurjchem-1150	165	5	,	,	PUNCT
eurjchem-1150	165	6	found	find	VERB
eurjchem-1150	165	7	:	:	PUNCT
eurjchem-1150	165	8	377.1987	377.1987	NUM
eurjchem-1150	165	9	.	.	NOUN
eurjchem-1150	165	10	2.2.9	2.2.9	NUM
eurjchem-1150	165	11	.	.	PUNCT
eurjchem-1150	166	1	synthesis	synthesis	NOUN
eurjchem-1150	166	2	of	of	ADP
eurjchem-1150	166	3	pectinolide	pectinolide	ADJ
eurjchem-1150	166	4	h	h	NOUN
eurjchem-1150	166	5	(	(	PUNCT
eurjchem-1150	166	6	1	1	NUM
eurjchem-1150	166	7	)	)	PUNCT
eurjchem-1150	166	8	and	and	CCONJ
eurjchem-1150	166	9	4‐epi‐pectinolide	4‐epi‐pectinolide	NUM
eurjchem-1150	166	10	h	h	NOUN
eurjchem-1150	166	11	(	(	PUNCT
eurjchem-1150	166	12	2	2	X
eurjchem-1150	166	13	)	)	PUNCT
eurjchem-1150	166	14	a	a	DET
eurjchem-1150	166	15	solution	solution	NOUN
eurjchem-1150	166	16	of	of	ADP
eurjchem-1150	166	17	compound	compound	NOUN
eurjchem-1150	166	18	15	15	NUM
eurjchem-1150	166	19	(	(	PUNCT
eurjchem-1150	166	20	25	25	NUM
eurjchem-1150	166	21	mg	mg	PROPN
eurjchem-1150	166	22	,	,	PUNCT
eurjchem-1150	166	23	0.706	0.706	NUM
eurjchem-1150	166	24	mmol	mmol	NOUN
eurjchem-1150	166	25	)	)	PUNCT
eurjchem-1150	166	26	in	in	ADP
eurjchem-1150	166	27	meoh	meoh	PROPN
eurjchem-1150	166	28	(	(	PUNCT
eurjchem-1150	166	29	10	10	NUM
eurjchem-1150	166	30	ml	ml	NOUN
eurjchem-1150	166	31	)	)	PUNCT
eurjchem-1150	166	32	was	be	AUX
eurjchem-1150	166	33	stirred	stir	VERB
eurjchem-1150	166	34	with	with	ADP
eurjchem-1150	166	35	a	a	DET
eurjchem-1150	166	36	catalytic	catalytic	ADJ
eurjchem-1150	166	37	amount	amount	NOUN
eurjchem-1150	166	38	of	of	ADP
eurjchem-1150	166	39	ptsa	ptsa	NOUN
eurjchem-1150	166	40	(	(	PUNCT
eurjchem-1150	166	41	2	2	NUM
eurjchem-1150	166	42	mg	mg	NOUN
eurjchem-1150	166	43	)	)	PUNCT
eurjchem-1150	166	44	at	at	ADP
eurjchem-1150	166	45	room	room	NOUN
eurjchem-1150	166	46	temperature	temperature	NOUN
eurjchem-1150	166	47	.	.	PUNCT
eurjchem-1150	167	1	after	after	SCONJ
eurjchem-1150	167	2	4	4	NUM
eurjchem-1150	167	3	h	h	NOUN
eurjchem-1150	167	4	meoh	meoh	NOUN
eurjchem-1150	167	5	was	be	AUX
eurjchem-1150	167	6	evaporated	evaporate	VERB
eurjchem-1150	167	7	and	and	CCONJ
eurjchem-1150	167	8	the	the	DET
eurjchem-1150	167	9	crude	crude	ADJ
eurjchem-1150	167	10	product	product	NOUN
eurjchem-1150	167	11	was	be	AUX
eurjchem-1150	167	12	purified	purify	VERB
eurjchem-1150	167	13	by	by	ADP
eurjchem-1150	167	14	preparative	preparative	ADJ
eurjchem-1150	167	15	thin	thin	ADJ
eurjchem-1150	167	16	layer	layer	NOUN
eurjchem-1150	167	17	chromatography	chromatography	NOUN
eurjchem-1150	167	18	(	(	PUNCT
eurjchem-1150	167	19	hexane	hexane	NOUN
eurjchem-1150	167	20	:	:	PUNCT
eurjchem-1150	167	21	etoac	etoac	ADJ
eurjchem-1150	167	22	,	,	PUNCT
eurjchem-1150	167	23	1:1	1:1	NUM
eurjchem-1150	167	24	,	,	PUNCT
eurjchem-1150	167	25	v	v	NOUN
eurjchem-1150	167	26	:	:	SYM
eurjchem-1150	167	27	v	v	NOUN
eurjchem-1150	167	28	)	)	PUNCT
eurjchem-1150	167	29	to	to	PART
eurjchem-1150	167	30	obtain	obtain	VERB
eurjchem-1150	167	31	pure	pure	ADJ
eurjchem-1150	167	32	compounds	compound	NOUN
eurjchem-1150	167	33	1	1	NUM
eurjchem-1150	167	34	and	and	CCONJ
eurjchem-1150	167	35	2	2	NUM
eurjchem-1150	167	36	in	in	ADP
eurjchem-1150	167	37	1.2	1.2	NUM
eurjchem-1150	167	38	:	:	SYM
eurjchem-1150	167	39	1	1	NUM
eurjchem-1150	167	40	ratio	ratio	NOUN
eurjchem-1150	167	41	(	(	PUNCT
eurjchem-1150	167	42	scheme	scheme	NOUN
eurjchem-1150	167	43	1	1	NUM
eurjchem-1150	167	44	)	)	PUNCT
eurjchem-1150	167	45	.	.	PUNCT
eurjchem-1150	168	1	(	(	PUNCT
eurjchem-1150	168	2	1s,4s	1s,4s	NUM
eurjchem-1150	168	3	,	,	PUNCT
eurjchem-1150	168	4	z)‐1‐hydroxy‐1‐((s)‐5‐oxo‐2,5‐dihydrofuran‐2‐yl)oct‐	z)‐1‐hydroxy‐1‐((s)‐5‐oxo‐2,5‐dihydrofuran‐2‐yl)oct‐	PROPN
eurjchem-1150	168	5	2‐en‐4‐yl	2‐en‐4‐yl	PROPN
eurjchem-1150	168	6	acetate	acetate	NOUN
eurjchem-1150	168	7	(	(	PUNCT
eurjchem-1150	168	8	pectinolide	pectinolide	PROPN
eurjchem-1150	168	9	h	h	NOUN
eurjchem-1150	168	10	)	)	PUNCT
eurjchem-1150	168	11	(	(	PUNCT
eurjchem-1150	168	12	1	1	NUM
eurjchem-1150	168	13	):	):	PUNCT
eurjchem-1150	168	14	color	color	NOUN
eurjchem-1150	168	15	:	:	PUNCT
eurjchem-1150	168	16	colorless	colorless	ADJ
eurjchem-1150	168	17	oil	oil	NOUN
eurjchem-1150	168	18	.	.	PUNCT
eurjchem-1150	169	1	yield	yield	NOUN
eurjchem-1150	169	2	:	:	PUNCT
eurjchem-1150	169	3	9.6	9.6	NUM
eurjchem-1150	169	4	mg	mg	NOUN
eurjchem-1150	169	5	,	,	PUNCT
eurjchem-1150	169	6	50.8	50.8	NUM
eurjchem-1150	169	7	%	%	NOUN
eurjchem-1150	169	8	.	.	PUNCT
eurjchem-1150	170	1	ft‐ir	ft‐ir	NOUN
eurjchem-1150	170	2	(	(	PUNCT
eurjchem-1150	170	3	neat	neat	ADJ
eurjchem-1150	170	4	,	,	PUNCT
eurjchem-1150	170	5	ν	ν	NOUN
eurjchem-1150	170	6	,	,	PUNCT
eurjchem-1150	170	7	cm‐1	cm‐1	PROPN
eurjchem-1150	170	8	):	):	PUNCT
eurjchem-1150	170	9	3439	3439	NUM
eurjchem-1150	170	10	,	,	PUNCT
eurjchem-1150	170	11	2931	2931	NUM
eurjchem-1150	170	12	,	,	PUNCT
eurjchem-1150	170	13	2862	2862	NUM
eurjchem-1150	170	14	,	,	PUNCT
eurjchem-1150	170	15	1750	1750	NUM
eurjchem-1150	170	16	,	,	PUNCT
eurjchem-1150	170	17	1241	1241	NUM
eurjchem-1150	170	18	,	,	PUNCT
eurjchem-1150	170	19	1042	1042	NUM
eurjchem-1150	170	20	.	.	PUNCT
eurjchem-1150	171	1	1h	1h	NUM
eurjchem-1150	171	2	nmr	nmr	NOUN
eurjchem-1150	171	3	(	(	PUNCT
eurjchem-1150	171	4	300	300	NUM
eurjchem-1150	171	5	mhz	mhz	NOUN
eurjchem-1150	171	6	,	,	PUNCT
eurjchem-1150	171	7	cdcl3	cdcl3	PROPN
eurjchem-1150	171	8	,	,	PUNCT
eurjchem-1150	171	9	δ	δ	PROPN
eurjchem-1150	171	10	,	,	PUNCT
eurjchem-1150	171	11	ppm	ppm	NOUN
eurjchem-1150	171	12	):	):	PUNCT
eurjchem-1150	171	13	0.89	0.89	NUM
eurjchem-1150	171	14	(	(	PUNCT
eurjchem-1150	171	15	t	t	PROPN
eurjchem-1150	171	16	,	,	PUNCT
eurjchem-1150	171	17	3h	3h	NUM
eurjchem-1150	171	18	,	,	PUNCT
eurjchem-1150	171	19	ch3‐(ch2)2	ch3‐(ch2)2	NOUN
eurjchem-1150	171	20	)	)	PUNCT
eurjchem-1150	171	21	,	,	PUNCT
eurjchem-1150	171	22	1.22‐1.36	1.22‐1.36	NUM
eurjchem-1150	171	23	(	(	PUNCT
eurjchem-1150	171	24	m	m	PROPN
eurjchem-1150	171	25	,	,	PUNCT
eurjchem-1150	171	26	4h	4h	NUM
eurjchem-1150	171	27	,	,	PUNCT
eurjchem-1150	171	28	(	(	PUNCT
eurjchem-1150	171	29	ch2)2‐ch3	ch2)2‐ch3	NUM
eurjchem-1150	171	30	)	)	PUNCT
eurjchem-1150	171	31	,	,	PUNCT
eurjchem-1150	171	32	1.50‐1.70	1.50‐1.70	NUM
eurjchem-1150	171	33	(	(	PUNCT
eurjchem-1150	171	34	m	m	PROPN
eurjchem-1150	171	35	,	,	PUNCT
eurjchem-1150	171	36	2h	2h	NUM
eurjchem-1150	171	37	,	,	PUNCT
eurjchem-1150	171	38	ch2‐(ch2)2‐ch3	ch2‐(ch2)2‐ch3	ADJ
eurjchem-1150	171	39	)	)	PUNCT
eurjchem-1150	171	40	,	,	PUNCT
eurjchem-1150	171	41	2.06	2.06	NUM
eurjchem-1150	171	42	(	(	PUNCT
eurjchem-1150	171	43	s	s	PROPN
eurjchem-1150	171	44	,	,	PUNCT
eurjchem-1150	171	45	3h	3h	NUM
eurjchem-1150	171	46	,	,	PUNCT
eurjchem-1150	171	47	ch3‐co	ch3‐co	NOUN
eurjchem-1150	171	48	)	)	PUNCT
eurjchem-1150	171	49	,	,	PUNCT
eurjchem-1150	171	50	3.07	3.07	NUM
eurjchem-1150	171	51	(	(	PUNCT
eurjchem-1150	171	52	br	br	PROPN
eurjchem-1150	171	53	.	.	PROPN
eurjchem-1150	171	54	1h	1h	NUM
eurjchem-1150	171	55	,	,	PUNCT
eurjchem-1150	171	56	oh	oh	INTJ
eurjchem-1150	171	57	)	)	PUNCT
eurjchem-1150	171	58	,	,	PUNCT
eurjchem-1150	171	59	4.28‐	4.28‐	NUM
eurjchem-1150	171	60	4.33	4.33	NUM
eurjchem-1150	171	61	(	(	PUNCT
eurjchem-1150	171	62	m	m	PROPN
eurjchem-1150	171	63	,	,	PUNCT
eurjchem-1150	171	64	1h	1h	NUM
eurjchem-1150	171	65	,	,	PUNCT
eurjchem-1150	171	66	ch‐oh	ch‐oh	NUM
eurjchem-1150	171	67	)	)	PUNCT
eurjchem-1150	171	68	,	,	PUNCT
eurjchem-1150	171	69	5.00‐5.04	5.00‐5.04	NUM
eurjchem-1150	171	70	(	(	PUNCT
eurjchem-1150	171	71	m	m	PROPN
eurjchem-1150	171	72	,	,	PUNCT
eurjchem-1150	171	73	1h	1h	NUM
eurjchem-1150	171	74	,	,	PUNCT
eurjchem-1150	171	75	ch(oac	ch(oac	NOUN
eurjchem-1150	171	76	)	)	PUNCT
eurjchem-1150	171	77	)	)	PUNCT
eurjchem-1150	171	78	,	,	PUNCT
eurjchem-1150	171	79	5.15‐5.22	5.15‐5.22	NUM
eurjchem-1150	171	80	(	(	PUNCT
eurjchem-1150	171	81	m	m	PROPN
eurjchem-1150	171	82	,	,	PUNCT
eurjchem-1150	171	83	1h	1h	NUM
eurjchem-1150	171	84	,	,	PUNCT
eurjchem-1150	171	85	ch‐ch	ch‐ch	NOUN
eurjchem-1150	171	86	=	=	NOUN
eurjchem-1150	171	87	ch‐coo	ch‐coo	NOUN
eurjchem-1150	171	88	)	)	PUNCT
eurjchem-1150	171	89	,	,	PUNCT
eurjchem-1150	171	90	5.62‐5.84	5.62‐5.84	PROPN
eurjchem-1150	171	91	(	(	PUNCT
eurjchem-1150	171	92	m	m	PROPN
eurjchem-1150	171	93	,	,	PUNCT
eurjchem-1150	171	94	2h	2h	NUM
eurjchem-1150	171	95	,	,	PUNCT
eurjchem-1150	171	96	ch	ch	NOUN
eurjchem-1150	171	97	=	=	NOUN
eurjchem-1150	171	98	ch‐ch(oac	ch‐ch(oac	X
eurjchem-1150	171	99	)	)	PUNCT
eurjchem-1150	171	100	)	)	PUNCT
eurjchem-1150	171	101	,	,	PUNCT
eurjchem-1150	171	102	6.19	6.19	NUM
eurjchem-1150	171	103	(	(	PUNCT
eurjchem-1150	171	104	dd	dd	PROPN
eurjchem-1150	171	105	,	,	PUNCT
eurjchem-1150	171	106	1h	1h	NUM
eurjchem-1150	171	107	,	,	PUNCT
eurjchem-1150	171	108	j	j	PROPN
eurjchem-1150	171	109	=	=	SYM
eurjchem-1150	171	110	4.5	4.5	NUM
eurjchem-1150	171	111	,	,	PUNCT
eurjchem-1150	171	112	1.5	1.5	NUM
eurjchem-1150	171	113	hz	hz	NOUN
eurjchem-1150	171	114	,	,	PUNCT
eurjchem-1150	171	115	=	=	SYM
eurjchem-1150	171	116	ch‐coo	ch‐coo	NOUN
eurjchem-1150	171	117	)	)	PUNCT
eurjchem-1150	171	118	,	,	PUNCT
eurjchem-1150	171	119	7.47	7.47	NUM
eurjchem-1150	171	120	(	(	PUNCT
eurjchem-1150	171	121	dd	dd	PROPN
eurjchem-1150	171	122	,	,	PUNCT
eurjchem-1150	171	123	1h	1h	NUM
eurjchem-1150	171	124	,	,	PUNCT
eurjchem-1150	171	125	j	j	PROPN
eurjchem-1150	171	126	=	=	SYM
eurjchem-1150	171	127	6.7	6.7	NUM
eurjchem-1150	171	128	,	,	PUNCT
eurjchem-1150	171	129	1.5	1.5	NUM
eurjchem-1150	171	130	hz	hz	NOUN
eurjchem-1150	171	131	,	,	PUNCT
eurjchem-1150	171	132	ch	ch	NOUN
eurjchem-1150	171	133	=	=	SYM
eurjchem-1150	171	134	ch‐coo	ch‐coo	NOUN
eurjchem-1150	171	135	)	)	PUNCT
eurjchem-1150	171	136	.	.	PUNCT
eurjchem-1150	172	1	13c	13c	NOUN
eurjchem-1150	172	2	nmr	nmr	NOUN
eurjchem-1150	172	3	(	(	PUNCT
eurjchem-1150	172	4	75	75	NUM
eurjchem-1150	172	5	mhz	mhz	NOUN
eurjchem-1150	172	6	,	,	PUNCT
eurjchem-1150	172	7	cdcl3	cdcl3	PROPN
eurjchem-1150	172	8	,	,	PUNCT
eurjchem-1150	172	9	δ	δ	PROPN
eurjchem-1150	172	10	,	,	PUNCT
eurjchem-1150	172	11	ppm	ppm	NUM
eurjchem-1150	172	12	):	):	PUNCT
eurjchem-1150	172	13	13.8	13.8	NUM
eurjchem-1150	172	14	,	,	PUNCT
eurjchem-1150	172	15	21.1	21.1	NUM
eurjchem-1150	172	16	,	,	PUNCT
eurjchem-1150	172	17	22.2	22.2	NUM
eurjchem-1150	172	18	,	,	PUNCT
eurjchem-1150	172	19	27.0	27.0	NUM
eurjchem-1150	172	20	,	,	PUNCT
eurjchem-1150	172	21	33.7	33.7	NUM
eurjchem-1150	172	22	,	,	PUNCT
eurjchem-1150	172	23	72.2	72.2	NUM
eurjchem-1150	172	24	,	,	PUNCT
eurjchem-1150	172	25	73.7	73.7	NUM
eurjchem-1150	172	26	,	,	PUNCT
eurjchem-1150	172	27	85.5	85.5	NUM
eurjchem-1150	172	28	,	,	PUNCT
eurjchem-1150	172	29	122.9	122.9	NUM
eurjchem-1150	172	30	,	,	PUNCT
eurjchem-1150	172	31	128.4	128.4	NUM
eurjchem-1150	172	32	,	,	PUNCT
eurjchem-1150	172	33	133.2	133.2	NUM
eurjchem-1150	172	34	,	,	PUNCT
eurjchem-1150	172	35	153.2	153.2	NUM
eurjchem-1150	172	36	,	,	PUNCT
eurjchem-1150	172	37	170.5	170.5	NUM
eurjchem-1150	172	38	,	,	PUNCT
eurjchem-1150	172	39	172.6	172.6	NUM
eurjchem-1150	172	40	.	.	PUNCT
eurjchem-1150	173	1	esi‐ms	esi‐ms	PROPN
eurjchem-1150	173	2	(	(	PUNCT
eurjchem-1150	173	3	m	m	PROPN
eurjchem-1150	173	4	/	/	SYM
eurjchem-1150	173	5	z	z	NOUN
eurjchem-1150	173	6	):	):	PUNCT
eurjchem-1150	173	7	291	291	NUM
eurjchem-1150	173	8	(	(	PUNCT
eurjchem-1150	173	9	m+na)+	m+na)+	NOUN
eurjchem-1150	173	10	.	.	PUNCT
eurjchem-1150	174	1	[	[	X
eurjchem-1150	174	2	α]d25	α]d25	NUM
eurjchem-1150	174	3	:	:	PUNCT
eurjchem-1150	174	4	‐39.0	‐39.0	X
eurjchem-1150	174	5	(	(	PUNCT
eurjchem-1150	174	6	c	c	NOUN
eurjchem-1150	174	7	0.32	0.32	NUM
eurjchem-1150	174	8	,	,	PUNCT
eurjchem-1150	174	9	chcl3	chcl3	PROPN
eurjchem-1150	174	10	)	)	PUNCT
eurjchem-1150	174	11	.	.	PUNCT
eurjchem-1150	175	1	hrms	hrm	VERB
eurjchem-1150	175	2	calcd	calcd	NOUN
eurjchem-1150	175	3	.	.	PUNCT
eurjchem-1150	176	1	for	for	ADP
eurjchem-1150	176	2	c14h20o5na	c14h20o5na	PROPN
eurjchem-1150	176	3	[	[	X
eurjchem-1150	176	4	m+na]+	m+na]+	NOUN
eurjchem-1150	176	5	:	:	PUNCT
eurjchem-1150	176	6	291.1202	291.1202	NUM
eurjchem-1150	176	7	;	;	PUNCT
eurjchem-1150	176	8	found	find	VERB
eurjchem-1150	176	9	:	:	PUNCT
eurjchem-1150	176	10	291.1200	291.1200	NUM
eurjchem-1150	176	11	.	.	PUNCT
eurjchem-1150	177	1	(	(	PUNCT
eurjchem-1150	177	2	1s,4r	1s,4r	NUM
eurjchem-1150	177	3	,	,	PUNCT
eurjchem-1150	177	4	z)‐1‐hydroxy‐1‐((s)‐5‐oxo‐2,5‐dihydrofuran‐2‐yl)oct‐	z)‐1‐hydroxy‐1‐((s)‐5‐oxo‐2,5‐dihydrofuran‐2‐yl)oct‐	PROPN
eurjchem-1150	177	5	2‐en‐4‐yl	2‐en‐4‐yl	NUM
eurjchem-1150	177	6	acetate	acetate	NOUN
eurjchem-1150	177	7	(	(	PUNCT
eurjchem-1150	177	8	4‐epi‐pectinolide	4‐epi‐pectinolide	NUM
eurjchem-1150	177	9	h	h	NOUN
eurjchem-1150	177	10	)	)	PUNCT
eurjchem-1150	177	11	(	(	PUNCT
eurjchem-1150	177	12	2	2	NUM
eurjchem-1150	177	13	):	):	PUNCT
eurjchem-1150	177	14	color	color	NOUN
eurjchem-1150	177	15	:	:	PUNCT
eurjchem-1150	177	16	colorless	colorless	ADJ
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eurjchem-1150	177	18	.	.	PUNCT
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eurjchem-1150	178	2	:	:	PUNCT
eurjchem-1150	178	3	8	8	NUM
eurjchem-1150	178	4	mg	mg	NUM
eurjchem-1150	178	5	,	,	PUNCT
eurjchem-1150	178	6	42.3	42.3	NUM
eurjchem-1150	178	7	%	%	NOUN
eurjchem-1150	178	8	.	.	PUNCT
eurjchem-1150	179	1	ft‐ir	ft‐ir	NOUN
eurjchem-1150	179	2	(	(	PUNCT
eurjchem-1150	179	3	neat	neat	ADJ
eurjchem-1150	179	4	,	,	PUNCT
eurjchem-1150	179	5	ν	ν	NOUN
eurjchem-1150	179	6	,	,	PUNCT
eurjchem-1150	179	7	cm‐1	cm‐1	PROPN
eurjchem-1150	179	8	):	):	PUNCT
eurjchem-1150	179	9	3444	3444	NUM
eurjchem-1150	179	10	,	,	PUNCT
eurjchem-1150	179	11	2928	2928	NUM
eurjchem-1150	179	12	,	,	PUNCT
eurjchem-1150	179	13	2856	2856	NUM
eurjchem-1150	179	14	,	,	PUNCT
eurjchem-1150	179	15	1750	1750	NUM
eurjchem-1150	179	16	,	,	PUNCT
eurjchem-1150	179	17	1241	1241	NUM
eurjchem-1150	179	18	,	,	PUNCT
eurjchem-1150	179	19	1043	1043	NUM
eurjchem-1150	179	20	.	.	PUNCT
eurjchem-1150	180	1	1h	1h	NUM
eurjchem-1150	180	2	nmr	nmr	NOUN
eurjchem-1150	180	3	(	(	PUNCT
eurjchem-1150	180	4	300	300	NUM
eurjchem-1150	180	5	mhz	mhz	NOUN
eurjchem-1150	180	6	,	,	PUNCT
eurjchem-1150	180	7	cdcl3	cdcl3	PROPN
eurjchem-1150	180	8	,	,	PUNCT
eurjchem-1150	180	9	δ	δ	PROPN
eurjchem-1150	180	10	,	,	PUNCT
eurjchem-1150	180	11	ppm	ppm	NOUN
eurjchem-1150	180	12	):	):	PUNCT
eurjchem-1150	180	13	0.89	0.89	NUM
eurjchem-1150	180	14	(	(	PUNCT
eurjchem-1150	180	15	t	t	PROPN
eurjchem-1150	180	16	,	,	PUNCT
eurjchem-1150	180	17	3h	3h	NUM
eurjchem-1150	180	18	,	,	PUNCT
eurjchem-1150	180	19	ch3‐(ch2)2	ch3‐(ch2)2	NOUN
eurjchem-1150	180	20	)	)	PUNCT
eurjchem-1150	180	21	,	,	PUNCT
eurjchem-1150	180	22	1.24‐1.31	1.24‐1.31	NUM
eurjchem-1150	180	23	(	(	PUNCT
eurjchem-1150	180	24	m	m	PROPN
eurjchem-1150	180	25	,	,	PUNCT
eurjchem-1150	180	26	4h	4h	NUM
eurjchem-1150	180	27	,	,	PUNCT
eurjchem-1150	180	28	(	(	PUNCT
eurjchem-1150	180	29	ch2)2‐ch3	ch2)2‐ch3	NUM
eurjchem-1150	180	30	)	)	PUNCT
eurjchem-1150	180	31	,	,	PUNCT
eurjchem-1150	180	32	1.54‐1.68	1.54‐1.68	NUM
eurjchem-1150	180	33	(	(	PUNCT
eurjchem-1150	180	34	m	m	PROPN
eurjchem-1150	180	35	,	,	PUNCT
eurjchem-1150	180	36	2h	2h	NUM
eurjchem-1150	180	37	,	,	PUNCT
eurjchem-1150	180	38	ch2‐(ch2)2‐ch3	ch2‐(ch2)2‐ch3	ADJ
eurjchem-1150	180	39	)	)	PUNCT
eurjchem-1150	180	40	,	,	PUNCT
eurjchem-1150	180	41	2.06	2.06	NUM
eurjchem-1150	180	42	(	(	PUNCT
eurjchem-1150	180	43	s	s	PROPN
eurjchem-1150	180	44	,	,	PUNCT
eurjchem-1150	180	45	3h	3h	NUM
eurjchem-1150	180	46	,	,	PUNCT
eurjchem-1150	180	47	ch3‐co	ch3‐co	NOUN
eurjchem-1150	180	48	)	)	PUNCT
eurjchem-1150	180	49	,	,	PUNCT
eurjchem-1150	180	50	2.76	2.76	NUM
eurjchem-1150	180	51	(	(	PUNCT
eurjchem-1150	180	52	br	br	PROPN
eurjchem-1150	180	53	.	.	PROPN
eurjchem-1150	180	54	1h	1h	NUM
eurjchem-1150	180	55	,	,	PUNCT
eurjchem-1150	180	56	oh	oh	INTJ
eurjchem-1150	180	57	)	)	PUNCT
eurjchem-1150	180	58	,	,	PUNCT
eurjchem-1150	180	59	4.27‐4.30	4.27‐4.30	NUM
eurjchem-1150	180	60	(	(	PUNCT
eurjchem-1150	180	61	m	m	PROPN
eurjchem-1150	180	62	,	,	PUNCT
eurjchem-1150	180	63	1h	1h	NUM
eurjchem-1150	180	64	,	,	PUNCT
eurjchem-1150	180	65	ch‐oh	ch‐oh	NUM
eurjchem-1150	180	66	)	)	PUNCT
eurjchem-1150	180	67	,	,	PUNCT
eurjchem-1150	180	68	4.99‐5.01	4.99‐5.01	NUM
eurjchem-1150	180	69	(	(	PUNCT
eurjchem-1150	180	70	m	m	PROPN
eurjchem-1150	180	71	,	,	PUNCT
eurjchem-1150	180	72	1h	1h	NUM
eurjchem-1150	180	73	,	,	PUNCT
eurjchem-1150	180	74	ch(oac	ch(oac	NOUN
eurjchem-1150	180	75	)	)	PUNCT
eurjchem-1150	180	76	)	)	PUNCT
eurjchem-1150	180	77	,	,	PUNCT
eurjchem-1150	180	78	5.18‐	5.18‐	NUM
eurjchem-1150	180	79	5.24	5.24	NUM
eurjchem-1150	180	80	(	(	PUNCT
eurjchem-1150	180	81	m	m	PROPN
eurjchem-1150	180	82	,	,	PUNCT
eurjchem-1150	180	83	1h	1h	NUM
eurjchem-1150	180	84	,	,	PUNCT
eurjchem-1150	180	85	ch‐ch	ch‐ch	NOUN
eurjchem-1150	180	86	=	=	NOUN
eurjchem-1150	180	87	ch‐coo	ch‐coo	NOUN
eurjchem-1150	180	88	)	)	PUNCT
eurjchem-1150	180	89	,	,	PUNCT
eurjchem-1150	180	90	5.64‐5.84	5.64‐5.84	NUM
eurjchem-1150	180	91	(	(	PUNCT
eurjchem-1150	180	92	m	m	PROPN
eurjchem-1150	180	93	,	,	PUNCT
eurjchem-1150	180	94	2h	2h	NUM
eurjchem-1150	180	95	,	,	PUNCT
eurjchem-1150	180	96	ch	ch	NOUN
eurjchem-1150	180	97	=	=	NOUN
eurjchem-1150	180	98	ch‐	ch‐	NOUN
eurjchem-1150	180	99	ch(oac	ch(oac	NOUN
eurjchem-1150	180	100	)	)	PUNCT
eurjchem-1150	180	101	)	)	PUNCT
eurjchem-1150	180	102	,	,	PUNCT
eurjchem-1150	180	103	6.18	6.18	NUM
eurjchem-1150	180	104	(	(	PUNCT
eurjchem-1150	180	105	d	d	PROPN
eurjchem-1150	180	106	,	,	PUNCT
eurjchem-1150	180	107	1h	1h	NUM
eurjchem-1150	180	108	,	,	PUNCT
eurjchem-1150	180	109	j	j	PROPN
eurjchem-1150	180	110	=	=	PROPN
eurjchem-1150	180	111	4.7	4.7	NUM
eurjchem-1150	180	112	hz	hz	NOUN
eurjchem-1150	180	113	,	,	PUNCT
eurjchem-1150	180	114	=	=	SYM
eurjchem-1150	180	115	ch‐coo	ch‐coo	NOUN
eurjchem-1150	180	116	)	)	PUNCT
eurjchem-1150	180	117	,	,	PUNCT
eurjchem-1150	180	118	7.43	7.43	NUM
eurjchem-1150	180	119	(	(	PUNCT
eurjchem-1150	180	120	dd	dd	PROPN
eurjchem-1150	180	121	,	,	PUNCT
eurjchem-1150	180	122	1h	1h	NUM
eurjchem-1150	180	123	,	,	PUNCT
eurjchem-1150	180	124	j	j	PROPN
eurjchem-1150	180	125	=	=	SYM
eurjchem-1150	180	126	5.7	5.7	NUM
eurjchem-1150	180	127	,	,	PUNCT
eurjchem-1150	180	128	4.7	4.7	NUM
eurjchem-1150	180	129	hz	hz	NOUN
eurjchem-1150	180	130	,	,	PUNCT
eurjchem-1150	180	131	ch	ch	NOUN
eurjchem-1150	180	132	=	=	SYM
eurjchem-1150	180	133	ch‐coo	ch‐coo	NOUN
eurjchem-1150	180	134	)	)	PUNCT
eurjchem-1150	180	135	.	.	PUNCT
eurjchem-1150	181	1	13c	13c	NOUN
eurjchem-1150	181	2	nmr	nmr	NOUN
eurjchem-1150	181	3	(	(	PUNCT
eurjchem-1150	181	4	75	75	NUM
eurjchem-1150	181	5	mhz	mhz	NOUN
eurjchem-1150	181	6	,	,	PUNCT
eurjchem-1150	181	7	cdcl3	cdcl3	PROPN
eurjchem-1150	181	8	,	,	PUNCT
eurjchem-1150	181	9	δ	δ	PROPN
eurjchem-1150	181	10	,	,	PUNCT
eurjchem-1150	181	11	ppm	ppm	NUM
eurjchem-1150	181	12	):	):	PUNCT
eurjchem-1150	181	13	13.8	13.8	NUM
eurjchem-1150	181	14	,	,	PUNCT
eurjchem-1150	181	15	21.2	21.2	NUM
eurjchem-1150	181	16	,	,	PUNCT
eurjchem-1150	181	17	22.3	22.3	NUM
eurjchem-1150	181	18	,	,	PUNCT
eurjchem-1150	181	19	27.1	27.1	NUM
eurjchem-1150	181	20	,	,	PUNCT
eurjchem-1150	181	21	33.8	33.8	NUM
eurjchem-1150	181	22	,	,	PUNCT
eurjchem-1150	181	23	72.5	72.5	NUM
eurjchem-1150	181	24	,	,	PUNCT
eurjchem-1150	181	25	73.7	73.7	NUM
eurjchem-1150	181	26	,	,	PUNCT
eurjchem-1150	181	27	85.5	85.5	NUM
eurjchem-1150	181	28	,	,	PUNCT
eurjchem-1150	181	29	123.0	123.0	NUM
eurjchem-1150	181	30	,	,	PUNCT
eurjchem-1150	181	31	128.3	128.3	NUM
eurjchem-1150	181	32	,	,	PUNCT
eurjchem-1150	181	33	133.5	133.5	NUM
eurjchem-1150	181	34	,	,	PUNCT
eurjchem-1150	181	35	153.1	153.1	NUM
eurjchem-1150	181	36	,	,	PUNCT
eurjchem-1150	181	37	170.5	170.5	NUM
eurjchem-1150	181	38	,	,	PUNCT
eurjchem-1150	181	39	172.5	172.5	NUM
eurjchem-1150	181	40	.	.	PUNCT
eurjchem-1150	182	1	esi‐ms	esi‐ms	PROPN
eurjchem-1150	182	2	(	(	PUNCT
eurjchem-1150	182	3	m	m	PROPN
eurjchem-1150	182	4	/	/	SYM
eurjchem-1150	182	5	z	z	NOUN
eurjchem-1150	182	6	):	):	PUNCT
eurjchem-1150	182	7	291	291	NUM
eurjchem-1150	182	8	(	(	PUNCT
eurjchem-1150	182	9	m+na)+	m+na)+	NOUN
eurjchem-1150	182	10	.	.	PUNCT
eurjchem-1150	183	1	[	[	X
eurjchem-1150	183	2	α]d25	α]d25	NUM
eurjchem-1150	183	3	:	:	PUNCT
eurjchem-1150	183	4	+21.9	+21.9	X
eurjchem-1150	183	5	(	(	PUNCT
eurjchem-1150	183	6	c	c	NOUN
eurjchem-1150	183	7	0.1	0.1	NUM
eurjchem-1150	183	8	,	,	PUNCT
eurjchem-1150	183	9	chcl3	chcl3	PROPN
eurjchem-1150	183	10	)	)	PUNCT
eurjchem-1150	183	11	.	.	PUNCT
eurjchem-1150	184	1	hrms	hrm	VERB
eurjchem-1150	184	2	calcd	calcd	NOUN
eurjchem-1150	184	3	.	.	PUNCT
eurjchem-1150	185	1	for	for	ADP
eurjchem-1150	185	2	c14h20o5na	c14h20o5na	PROPN
eurjchem-1150	185	3	[	[	X
eurjchem-1150	185	4	m+na]+	m+na]+	NOUN
eurjchem-1150	185	5	:	:	PUNCT
eurjchem-1150	185	6	291.1202	291.1202	NUM
eurjchem-1150	185	7	,	,	PUNCT
eurjchem-1150	185	8	found	find	VERB
eurjchem-1150	185	9	:	:	PUNCT
eurjchem-1150	185	10	291.1188	291.1188	NUM
eurjchem-1150	185	11	.	.	NOUN
eurjchem-1150	185	12	3	3	NUM
eurjchem-1150	185	13	.	.	NOUN
eurjchem-1150	185	14	results	result	NOUN
eurjchem-1150	185	15	and	and	CCONJ
eurjchem-1150	185	16	discussion	discussion	NOUN
eurjchem-1150	185	17	a	a	DET
eurjchem-1150	185	18	cursory	cursory	NOUN
eurjchem-1150	185	19	look	look	NOUN
eurjchem-1150	185	20	at	at	ADP
eurjchem-1150	185	21	the	the	DET
eurjchem-1150	185	22	structure	structure	NOUN
eurjchem-1150	185	23	of	of	ADP
eurjchem-1150	185	24	compound	compound	NOUN
eurjchem-1150	185	25	1	1	NUM
eurjchem-1150	185	26	shows	show	VERB
eurjchem-1150	185	27	that	that	SCONJ
eurjchem-1150	185	28	(	(	PUNCT
eurjchem-1150	185	29	+	+	NOUN
eurjchem-1150	185	30	)	)	PUNCT
eurjchem-1150	185	31	‐diethyl	‐diethyl	PROPN
eurjchem-1150	185	32	l‐tartrate	l‐tartrate	PUNCT
eurjchem-1150	185	33	(	(	PUNCT
eurjchem-1150	185	34	6	6	X
eurjchem-1150	185	35	)	)	PUNCT
eurjchem-1150	185	36	possesses	possess	VERB
eurjchem-1150	185	37	the	the	DET
eurjchem-1150	185	38	required	require	VERB
eurjchem-1150	185	39	(	(	PUNCT
eurjchem-1150	185	40	2s,3s)‐	2s,3s)‐	NUM
eurjchem-1150	185	41	stereochemistry	stereochemistry	NOUN
eurjchem-1150	185	42	.	.	PUNCT
eurjchem-1150	186	1	protection	protection	NOUN
eurjchem-1150	186	2	of	of	ADP
eurjchem-1150	186	3	the	the	DET
eurjchem-1150	186	4	vicinal	vicinal	ADJ
eurjchem-1150	186	5	hydroxy	hydroxy	NOUN
eurjchem-1150	186	6	groups	group	NOUN
eurjchem-1150	186	7	as	as	ADP
eurjchem-1150	186	8	an	an	DET
eurjchem-1150	186	9	acetonide	acetonide	NOUN
eurjchem-1150	186	10	and	and	CCONJ
eurjchem-1150	186	11	reduction	reduction	NOUN
eurjchem-1150	186	12	of	of	ADP
eurjchem-1150	186	13	compound	compound	NOUN
eurjchem-1150	186	14	7	7	NUM
eurjchem-1150	186	15	with	with	ADP
eurjchem-1150	186	16	lialh4	lialh4	NOUN
eurjchem-1150	186	17	gave	give	VERB
eurjchem-1150	186	18	the	the	DET
eurjchem-1150	186	19	corresponding	corresponding	ADJ
eurjchem-1150	186	20	diol	diol	NOUN
eurjchem-1150	186	21	(	(	PUNCT
eurjchem-1150	186	22	8)	8)	NUM
eurjchem-1150	186	23	in	in	ADP
eurjchem-1150	186	24	85	85	NUM
eurjchem-1150	186	25	%	%	NOUN
eurjchem-1150	186	26	yield	yield	NOUN
eurjchem-1150	186	27	.	.	PUNCT
eurjchem-1150	187	1	selective	selective	ADJ
eurjchem-1150	187	2	mono‐	mono‐	NOUN
eurjchem-1150	187	3	protection	protection	NOUN
eurjchem-1150	187	4	of	of	ADP
eurjchem-1150	187	5	compound	compound	NOUN
eurjchem-1150	187	6	8	8	NUM
eurjchem-1150	187	7	was	be	AUX
eurjchem-1150	187	8	achieved	achieve	VERB
eurjchem-1150	187	9	with	with	ADP
eurjchem-1150	187	10	1	1	NUM
eurjchem-1150	187	11	equiv	equiv	NOUN
eurjchem-1150	187	12	.	.	PUNCT
eurjchem-1150	188	1	of	of	ADP
eurjchem-1150	188	2	(	(	PUNCT
eurjchem-1150	188	3	tert‐	tert‐	PROPN
eurjchem-1150	188	4	butyl	butyl	NOUN
eurjchem-1150	188	5	diphenylsilyl	diphenylsilyl	PROPN
eurjchem-1150	188	6	chloride	chloride	NOUN
eurjchem-1150	188	7	(	(	PUNCT
eurjchem-1150	188	8	tbdpscl	tbdpscl	NOUN
eurjchem-1150	188	9	)	)	PUNCT
eurjchem-1150	188	10	in	in	ADP
eurjchem-1150	188	11	presence	presence	NOUN
eurjchem-1150	188	12	of	of	ADP
eurjchem-1150	188	13	nah	nah	INTJ
eurjchem-1150	188	14	in	in	ADP
eurjchem-1150	188	15	thf	thf	NOUN
eurjchem-1150	188	16	.	.	PUNCT
eurjchem-1150	189	1	the	the	DET
eurjchem-1150	189	2	mono	mono	PROPN
eurjchem-1150	189	3	protected	protect	VERB
eurjchem-1150	189	4	alcohol	alcohol	NOUN
eurjchem-1150	189	5	(	(	PUNCT
eurjchem-1150	189	6	9	9	NUM
eurjchem-1150	189	7	)	)	PUNCT
eurjchem-1150	189	8	was	be	AUX
eurjchem-1150	189	9	oxidized	oxidize	VERB
eurjchem-1150	189	10	to	to	ADP
eurjchem-1150	189	11	the	the	DET
eurjchem-1150	189	12	corresponding	correspond	VERB
eurjchem-1150	189	13	aldehyde	aldehyde	NOUN
eurjchem-1150	189	14	by	by	ADP
eurjchem-1150	189	15	swern	swern	ADJ
eurjchem-1150	189	16	oxidation	oxidation	NOUN
eurjchem-1150	189	17	.	.	PUNCT
eurjchem-1150	190	1	the	the	DET
eurjchem-1150	190	2	crude	crude	ADJ
eurjchem-1150	190	3	aldehyde	aldehyde	NOUN
eurjchem-1150	190	4	was	be	AUX
eurjchem-1150	190	5	subjected	subject	VERB
eurjchem-1150	190	6	to	to	ADP
eurjchem-1150	190	7	wittig	wittig	NOUN
eurjchem-1150	190	8	olefination	olefination	NOUN
eurjchem-1150	190	9	in	in	ADP
eurjchem-1150	190	10	methanol	methanol	NOUN
eurjchem-1150	190	11	to	to	PART
eurjchem-1150	190	12	obtain	obtain	VERB
eurjchem-1150	190	13	a	a	DET
eurjchem-1150	190	14	mixture	mixture	NOUN
eurjchem-1150	190	15	of	of	ADP
eurjchem-1150	190	16	e	e	NOUN
eurjchem-1150	190	17	and	and	CCONJ
eurjchem-1150	190	18	z‐alkene	z‐alkene	NUM
eurjchem-1150	190	19	(	(	PUNCT
eurjchem-1150	190	20	10	10	NUM
eurjchem-1150	190	21	)	)	PUNCT
eurjchem-1150	190	22	with	with	ADP
eurjchem-1150	190	23	e	e	PRON
eurjchem-1150	190	24	to	to	ADP
eurjchem-1150	190	25	z	z	NOUN
eurjchem-1150	190	26	ratio	ratio	NOUN
eurjchem-1150	190	27	of	of	ADP
eurjchem-1150	190	28	20:80	20:80	NUM
eurjchem-1150	190	29	.	.	PUNCT
eurjchem-1150	191	1	the	the	DET
eurjchem-1150	191	2	isomers	isomer	NOUN
eurjchem-1150	191	3	were	be	AUX
eurjchem-1150	191	4	easily	easily	ADV
eurjchem-1150	191	5	separated	separate	VERB
eurjchem-1150	191	6	by	by	ADP
eurjchem-1150	191	7	column	column	NOUN
eurjchem-1150	191	8	chromatography	chromatography	NOUN
eurjchem-1150	191	9	[	[	X
eurjchem-1150	191	10	13	13	NUM
eurjchem-1150	191	11	]	]	PUNCT
eurjchem-1150	191	12	.	.	PUNCT
eurjchem-1150	192	1	reduction	reduction	NOUN
eurjchem-1150	192	2	of	of	ADP
eurjchem-1150	192	3	the	the	DET
eurjchem-1150	192	4	ester	ester	NOUN
eurjchem-1150	192	5	group	group	NOUN
eurjchem-1150	192	6	of	of	ADP
eurjchem-1150	192	7	z‐(10a	z‐(10a	PROPN
eurjchem-1150	192	8	)	)	PUNCT
eurjchem-1150	192	9	with	with	ADP
eurjchem-1150	192	10	dibal‐h	dibal‐h	NOUN
eurjchem-1150	192	11	in	in	ADP
eurjchem-1150	192	12	ch2cl2	ch2cl2	NOUN
eurjchem-1150	192	13	and	and	CCONJ
eurjchem-1150	192	14	grignard	grignard	ADJ
eurjchem-1150	192	15	reaction	reaction	NOUN
eurjchem-1150	192	16	of	of	ADP
eurjchem-1150	192	17	the	the	DET
eurjchem-1150	192	18	aldehyde	aldehyde	NOUN
eurjchem-1150	192	19	(	(	PUNCT
eurjchem-1150	192	20	11	11	NUM
eurjchem-1150	192	21	)	)	PUNCT
eurjchem-1150	192	22	with	with	ADP
eurjchem-1150	192	23	n‐butyl	n‐butyl	PUNCT
eurjchem-1150	192	24	magnesium	magnesium	NOUN
eurjchem-1150	192	25	bromide	bromide	NOUN
eurjchem-1150	192	26	gave	give	VERB
eurjchem-1150	192	27	a	a	DET
eurjchem-1150	192	28	diastereo‐	diastereo‐	NOUN
eurjchem-1150	192	29	isomeric	isomeric	ADJ
eurjchem-1150	192	30	mixture	mixture	NOUN
eurjchem-1150	192	31	of	of	ADP
eurjchem-1150	192	32	secondary	secondary	ADJ
eurjchem-1150	192	33	alcohols	alcohol	NOUN
eurjchem-1150	192	34	(	(	PUNCT
eurjchem-1150	192	35	12	12	NUM
eurjchem-1150	192	36	)	)	PUNCT
eurjchem-1150	192	37	.	.	PUNCT
eurjchem-1150	193	1	acetylation	acetylation	NOUN
eurjchem-1150	193	2	with	with	ADP
eurjchem-1150	193	3	ac2o	ac2o	PROPN
eurjchem-1150	193	4	in	in	ADP
eurjchem-1150	193	5	pyridine	pyridine	NOUN
eurjchem-1150	193	6	provided	provide	VERB
eurjchem-1150	193	7	a	a	DET
eurjchem-1150	193	8	mixture	mixture	NOUN
eurjchem-1150	193	9	of	of	ADP
eurjchem-1150	193	10	diastereomers	diastereomer	NOUN
eurjchem-1150	193	11	(	(	PUNCT
eurjchem-1150	193	12	13	13	NUM
eurjchem-1150	193	13	)	)	PUNCT
eurjchem-1150	193	14	.	.	PUNCT
eurjchem-1150	194	1	deprotection	deprotection	NOUN
eurjchem-1150	194	2	of	of	ADP
eurjchem-1150	194	3	the	the	DET
eurjchem-1150	194	4	primary	primary	ADJ
eurjchem-1150	194	5	alcohol	alcohol	NOUN
eurjchem-1150	194	6	with	with	ADP
eurjchem-1150	194	7	tbaf	tbaf	PROPN
eurjchem-1150	194	8	followed	follow	VERB
eurjchem-1150	194	9	by	by	ADP
eurjchem-1150	194	10	swern	swern	ADJ
eurjchem-1150	194	11	oxidation	oxidation	NOUN
eurjchem-1150	194	12	of	of	ADP
eurjchem-1150	194	13	the	the	DET
eurjchem-1150	194	14	alcohol	alcohol	NOUN
eurjchem-1150	194	15	(	(	PUNCT
eurjchem-1150	194	16	14	14	NUM
eurjchem-1150	194	17	)	)	PUNCT
eurjchem-1150	194	18	gave	give	VERB
eurjchem-1150	194	19	an	an	DET
eurjchem-1150	194	20	intermediate	intermediate	ADJ
eurjchem-1150	194	21	aldehyde	aldehyde	NOUN
eurjchem-1150	194	22	which	which	PRON
eurjchem-1150	194	23	was	be	AUX
eurjchem-1150	194	24	subjected	subject	VERB
eurjchem-1150	194	25	to	to	ADP
eurjchem-1150	194	26	still‐gennari	still‐gennari	ADJ
eurjchem-1150	194	27	olefination	olefination	NOUN
eurjchem-1150	194	28	reaction	reaction	NOUN
eurjchem-1150	195	1	[	[	X
eurjchem-1150	195	2	14,15	14,15	NUM
eurjchem-1150	195	3	]	]	PUNCT
eurjchem-1150	195	4	without	without	ADP
eurjchem-1150	195	5	isolation	isolation	NOUN
eurjchem-1150	195	6	to	to	PART
eurjchem-1150	195	7	afford	afford	VERB
eurjchem-1150	195	8	the	the	DET
eurjchem-1150	195	9	corresponding	corresponding	ADJ
eurjchem-1150	195	10	α	α	PROPN
eurjchem-1150	195	11	,	,	PUNCT
eurjchem-1150	195	12	β‐unsaturated	β‐unsaturate	VERB
eurjchem-1150	195	13	ester	ester	NOUN
eurjchem-1150	195	14	(	(	PUNCT
eurjchem-1150	195	15	15	15	NUM
eurjchem-1150	195	16	)	)	PUNCT
eurjchem-1150	195	17	in	in	ADP
eurjchem-1150	195	18	80	80	NUM
eurjchem-1150	195	19	%	%	NOUN
eurjchem-1150	195	20	yield	yield	NOUN
eurjchem-1150	195	21	.	.	PUNCT
eurjchem-1150	196	1	deprotection	deprotection	NOUN
eurjchem-1150	196	2	of	of	ADP
eurjchem-1150	196	3	the	the	DET
eurjchem-1150	196	4	acetonide	acetonide	NOUN
eurjchem-1150	196	5	and	and	CCONJ
eurjchem-1150	196	6	subsequent	subsequent	ADJ
eurjchem-1150	196	7	in	in	ADP
eurjchem-1150	196	8	situ	situ	ADJ
eurjchem-1150	196	9	lactonization	lactonization	NOUN
eurjchem-1150	196	10	of	of	ADP
eurjchem-1150	196	11	ester	ester	NOUN
eurjchem-1150	196	12	(	(	PUNCT
eurjchem-1150	196	13	15	15	NUM
eurjchem-1150	196	14	)	)	PUNCT
eurjchem-1150	196	15	with	with	ADP
eurjchem-1150	196	16	p‐toluenesulfonic	p‐toluenesulfonic	PUNCT
eurjchem-1150	196	17	acid	acid	NOUN
eurjchem-1150	196	18	in	in	ADP
eurjchem-1150	196	19	meoh	meoh	PROPN
eurjchem-1150	196	20	afforded	afford	VERB
eurjchem-1150	196	21	a	a	DET
eurjchem-1150	196	22	diastereomeric	diastereomeric	ADJ
eurjchem-1150	196	23	mixture	mixture	NOUN
eurjchem-1150	196	24	of	of	ADP
eurjchem-1150	196	25	pectinolide	pectinolide	ADJ
eurjchem-1150	196	26	h	h	NOUN
eurjchem-1150	196	27	(	(	PUNCT
eurjchem-1150	196	28	1	1	NUM
eurjchem-1150	196	29	)	)	PUNCT
eurjchem-1150	196	30	and	and	CCONJ
eurjchem-1150	196	31	4'‐epi‐pectinolide	4'‐epi‐pectinolide	NUM
eurjchem-1150	196	32	h	h	NOUN
eurjchem-1150	196	33	(	(	PUNCT
eurjchem-1150	196	34	2	2	NUM
eurjchem-1150	196	35	)	)	PUNCT
eurjchem-1150	196	36	in	in	ADP
eurjchem-1150	196	37	98	98	NUM
eurjchem-1150	196	38	%	%	NOUN
eurjchem-1150	196	39	yield	yield	NOUN
eurjchem-1150	196	40	(	(	PUNCT
eurjchem-1150	196	41	scheme	scheme	NOUN
eurjchem-1150	196	42	1	1	NUM
eurjchem-1150	196	43	)	)	PUNCT
eurjchem-1150	196	44	.	.	PUNCT
eurjchem-1150	197	1	both	both	CCONJ
eurjchem-1150	197	2	the	the	DET
eurjchem-1150	197	3	diastereomers	diastereomer	NOUN
eurjchem-1150	197	4	were	be	AUX
eurjchem-1150	197	5	separa‐	separa‐	PROPN
eurjchem-1150	197	6	ted	te	VERB
eurjchem-1150	197	7	by	by	ADP
eurjchem-1150	197	8	preparative	preparative	ADJ
eurjchem-1150	197	9	tlc	tlc	NOUN
eurjchem-1150	197	10	.	.	PUNCT
eurjchem-1150	198	1	the	the	DET
eurjchem-1150	198	2	1h	1h	NUM
eurjchem-1150	198	3	and	and	CCONJ
eurjchem-1150	198	4	13c	13c	NOUN
eurjchem-1150	198	5	nmr	nmr	NOUN
eurjchem-1150	198	6	spectral	spectral	ADJ
eurjchem-1150	198	7	data	datum	NOUN
eurjchem-1150	198	8	and	and	CCONJ
eurjchem-1150	198	9	optical	optical	ADJ
eurjchem-1150	198	10	rotation	rotation	NOUN
eurjchem-1150	198	11	of	of	ADP
eurjchem-1150	198	12	pectinolide	pectinolide	ADJ
eurjchem-1150	198	13	h	h	NOUN
eurjchem-1150	198	14	were	be	AUX
eurjchem-1150	198	15	in	in	ADP
eurjchem-1150	198	16	excellent	excellent	ADJ
eurjchem-1150	198	17	agreement	agreement	NOUN
eurjchem-1150	198	18	with	with	ADP
eurjchem-1150	198	19	the	the	DET
eurjchem-1150	198	20	data	datum	NOUN
eurjchem-1150	198	21	previously	previously	ADV
eurjchem-1150	198	22	reported	report	VERB
eurjchem-1150	198	23	in	in	ADP
eurjchem-1150	198	24	literature	literature	NOUN
eurjchem-1150	198	25	[	[	X
eurjchem-1150	198	26	11,12	11,12	NUM
eurjchem-1150	198	27	]	]	PUNCT
eurjchem-1150	198	28	.	.	PUNCT
eurjchem-1150	199	1	4	4	X
eurjchem-1150	199	2	.	.	X
eurjchem-1150	199	3	conclusion	conclusion	NOUN
eurjchem-1150	199	4	in	in	ADP
eurjchem-1150	199	5	conclusion	conclusion	NOUN
eurjchem-1150	199	6	,	,	PUNCT
eurjchem-1150	199	7	a	a	DET
eurjchem-1150	199	8	simple	simple	ADJ
eurjchem-1150	199	9	stereoselective	stereoselective	ADJ
eurjchem-1150	199	10	total	total	ADJ
eurjchem-1150	199	11	synthesis	synthesis	NOUN
eurjchem-1150	199	12	of	of	ADP
eurjchem-1150	199	13	pectinolide	pectinolide	ADJ
eurjchem-1150	199	14	h	h	NOUN
eurjchem-1150	199	15	and	and	CCONJ
eurjchem-1150	199	16	4'‐epi‐pectinolide	4'‐epi‐pectinolide	PROPN
eurjchem-1150	199	17	h	h	NOUN
eurjchem-1150	199	18	have	have	AUX
eurjchem-1150	199	19	been	be	AUX
eurjchem-1150	199	20	achieved	achieve	VERB
eurjchem-1150	199	21	from	from	ADP
eurjchem-1150	199	22	(	(	PUNCT
eurjchem-1150	199	23	+	+	NOUN
eurjchem-1150	199	24	)	)	PUNCT
eurjchem-1150	199	25	‐det	‐det	ADJ
eurjchem-1150	199	26	in	in	ADP
eurjchem-1150	199	27	nine	nine	NUM
eurjchem-1150	199	28	steps	step	NOUN
eurjchem-1150	199	29	with	with	ADP
eurjchem-1150	199	30	27	27	NUM
eurjchem-1150	199	31	%	%	NOUN
eurjchem-1150	199	32	overall	overall	ADJ
eurjchem-1150	199	33	yield	yield	NOUN
eurjchem-1150	199	34	.	.	PUNCT
eurjchem-1150	200	1	our	our	PRON
eurjchem-1150	200	2	synthetic	synthetic	ADJ
eurjchem-1150	200	3	strategy	strategy	NOUN
eurjchem-1150	200	4	provides	provide	VERB
eurjchem-1150	200	5	pectinolide	pectinolide	ADJ
eurjchem-1150	200	6	h	h	NOUN
eurjchem-1150	200	7	and	and	CCONJ
eurjchem-1150	200	8	the	the	DET
eurjchem-1150	200	9	epimer	epimer	NOUN
eurjchem-1150	200	10	4'‐	4'‐	X
eurjchem-1150	200	11	epi‐pectinolide	epi‐pectinolide	NOUN
eurjchem-1150	200	12	h.	h.	PROPN
eurjchem-1150	200	13	acknowledgements	acknowledgement	NOUN
eurjchem-1150	200	14	the	the	DET
eurjchem-1150	200	15	authors	author	NOUN
eurjchem-1150	200	16	thank	thank	VERB
eurjchem-1150	200	17	university	university	PROPN
eurjchem-1150	200	18	grants	grant	NOUN
eurjchem-1150	200	19	commission	commission	PROPN
eurjchem-1150	200	20	for	for	ADP
eurjchem-1150	200	21	grant	grant	NOUN
eurjchem-1150	200	22	of	of	ADP
eurjchem-1150	200	23	senior	senior	ADJ
eurjchem-1150	200	24	research	research	NOUN
eurjchem-1150	200	25	fellowship	fellowship	NOUN
eurjchem-1150	200	26	to	to	PART
eurjchem-1150	200	27	pr	pr	VERB
eurjchem-1150	200	28	and	and	CCONJ
eurjchem-1150	200	29	council	council	PROPN
eurjchem-1150	200	30	of	of	ADP
eurjchem-1150	200	31	scientific	scientific	ADJ
eurjchem-1150	200	32	and	and	CCONJ
eurjchem-1150	200	33	industrial	industrial	ADJ
eurjchem-1150	200	34	research	research	NOUN
eurjchem-1150	200	35	,	,	PUNCT
eurjchem-1150	200	36	new	new	ADJ
eurjchem-1150	200	37	delhi	delhi	PROPN
eurjchem-1150	200	38	for	for	ADP
eurjchem-1150	200	39	financial	financial	ADJ
eurjchem-1150	200	40	assistance	assistance	NOUN
eurjchem-1150	200	41	under	under	ADP
eurjchem-1150	200	42	xii	xii	NOUN
eurjchem-1150	200	43	5	5	NUM
eurjchem-1150	200	44	year	year	NOUN
eurjchem-1150	200	45	plan	plan	NOUN
eurjchem-1150	200	46	csc0108‐origin	csc0108‐origin	NOUN
eurjchem-1150	200	47	.	.	PUNCT
eurjchem-1150	201	1	references	reference	NOUN
eurjchem-1150	201	2	[	[	X
eurjchem-1150	201	3	1	1	NUM
eurjchem-1150	201	4	]	]	PUNCT
eurjchem-1150	201	5	.	.	PUNCT
eurjchem-1150	202	1	fragoso‐serrano	fragoso‐serrano	ADJ
eurjchem-1150	202	2	,	,	PUNCT
eurjchem-1150	202	3	m.	m.	NOUN
eurjchem-1150	202	4	;	;	PUNCT
eurjchem-1150	202	5	gibbons	gibbon	NOUN
eurjchem-1150	202	6	,	,	PUNCT
eurjchem-1150	202	7	s.	s.	PROPN
eurjchem-1150	202	8	;	;	PUNCT
eurjchem-1150	202	9	perda‐miranda	perda‐miranda	PROPN
eurjchem-1150	202	10	,	,	PUNCT
eurjchem-1150	202	11	r.	r.	PROPN
eurjchem-1150	202	12	planta	planta	PROPN
eurjchem-1150	202	13	med	med	PROPN
eurjchem-1150	202	14	.	.	PUNCT
eurjchem-1150	203	1	2005	2005	NUM
eurjchem-1150	203	2	,	,	PUNCT
eurjchem-1150	203	3	71	71	NUM
eurjchem-1150	203	4	,	,	PUNCT
eurjchem-1150	203	5	278‐280	278‐280	NUM
eurjchem-1150	203	6	.	.	PUNCT
eurjchem-1150	204	1	[	[	X
eurjchem-1150	204	2	2	2	NUM
eurjchem-1150	204	3	]	]	PUNCT
eurjchem-1150	204	4	.	.	PUNCT
eurjchem-1150	205	1	hentzer	hentzer	PROPN
eurjchem-1150	205	2	,	,	PUNCT
eurjchem-1150	205	3	m.	m.	NOUN
eurjchem-1150	205	4	;	;	PUNCT
eurjchem-1150	205	5	eberl	eberl	PROPN
eurjchem-1150	205	6	,	,	PUNCT
eurjchem-1150	205	7	l.	l.	PROPN
eurjchem-1150	205	8	;	;	PUNCT
eurjchem-1150	205	9	nielsen	nielsen	PROPN
eurjchem-1150	205	10	,	,	PUNCT
eurjchem-1150	205	11	j.	j.	PROPN
eurjchem-1150	205	12	;	;	PUNCT
eurjchem-1150	205	13	giviskov	giviskov	PROPN
eurjchem-1150	205	14	,	,	PUNCT
eurjchem-1150	205	15	m.	m.	NOUN
eurjchem-1150	205	16	biodrugs	biodrug	NOUN
eurjchem-1150	205	17	2003	2003	NUM
eurjchem-1150	205	18	,	,	PUNCT
eurjchem-1150	205	19	17	17	NUM
eurjchem-1150	205	20	,	,	PUNCT
eurjchem-1150	205	21	241‐	241‐	NUM
eurjchem-1150	205	22	250	250	NUM
eurjchem-1150	205	23	.	.	PUNCT
eurjchem-1150	206	1	[	[	X
eurjchem-1150	206	2	3	3	NUM
eurjchem-1150	206	3	]	]	PUNCT
eurjchem-1150	206	4	.	.	PUNCT
eurjchem-1150	207	1	hjelmgaard	hjelmgaard	NOUN
eurjchem-1150	207	2	,	,	PUNCT
eurjchem-1150	207	3	t.	t.	PROPN
eurjchem-1150	207	4	;	;	PUNCT
eurjchem-1150	207	5	persson	persson	PROPN
eurjchem-1150	207	6	,	,	PUNCT
eurjchem-1150	207	7	t.	t.	PROPN
eurjchem-1150	207	8	;	;	PUNCT
eurjchem-1150	207	9	rasmussen	rasmussen	PROPN
eurjchem-1150	207	10	,	,	PUNCT
eurjchem-1150	207	11	t.	t.	PROPN
eurjchem-1150	207	12	b.	b.	PROPN
eurjchem-1150	207	13	;	;	PUNCT
eurjchem-1150	207	14	givskov	givskov	PROPN
eurjchem-1150	207	15	,	,	PUNCT
eurjchem-1150	207	16	m.	m.	NOUN
eurjchem-1150	207	17	;	;	PUNCT
eurjchem-1150	207	18	nielsen	nielsen	PROPN
eurjchem-1150	207	19	.	.	PUNCT
eurjchem-1150	208	1	j.	j.	PROPN
eurjchem-1150	208	2	bioorg	bioorg	PROPN
eurjchem-1150	208	3	.	.	PUNCT
eurjchem-1150	209	1	med	med	PROPN
eurjchem-1150	209	2	.	.	PROPN
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eurjchem-1150	209	4	.	.	PUNCT
eurjchem-1150	210	1	2003	2003	NUM
eurjchem-1150	210	2	,	,	PUNCT
eurjchem-1150	210	3	11	11	NUM
eurjchem-1150	210	4	,	,	PUNCT
eurjchem-1150	210	5	3261‐3271	3261‐3271	NUM
eurjchem-1150	210	6	.	.	PUNCT
eurjchem-1150	211	1	[	[	X
eurjchem-1150	211	2	4	4	NUM
eurjchem-1150	211	3	]	]	PUNCT
eurjchem-1150	211	4	.	.	PUNCT
eurjchem-1150	211	5	fusetani	fusetani	PROPN
eurjchem-1150	211	6	,	,	PUNCT
eurjchem-1150	211	7	n.	n.	PROPN
eurjchem-1150	211	8	nat	nat	PROPN
eurjchem-1150	211	9	.	.	PUNCT
eurjchem-1150	212	1	prod	prod	PROPN
eurjchem-1150	212	2	.	.	PUNCT
eurjchem-1150	213	1	rep	rep	PROPN
eurjchem-1150	213	2	.	.	PROPN
eurjchem-1150	213	3	2004	2004	NUM
eurjchem-1150	213	4	,	,	PUNCT
eurjchem-1150	213	5	21	21	NUM
eurjchem-1150	213	6	,	,	PUNCT
eurjchem-1150	213	7	94‐104	94‐104	NOUN
eurjchem-1150	213	8	.	.	PUNCT
eurjchem-1150	214	1	[	[	X
eurjchem-1150	214	2	5	5	NUM
eurjchem-1150	214	3	]	]	PUNCT
eurjchem-1150	214	4	.	.	PUNCT
eurjchem-1150	214	5	cateni	cateni	PROPN
eurjchem-1150	214	6	,	,	PUNCT
eurjchem-1150	214	7	f.	f.	PROPN
eurjchem-1150	214	8	;	;	PUNCT
eurjchem-1150	214	9	zillic	zillic	PROPN
eurjchem-1150	214	10	,	,	PUNCT
eurjchem-1150	214	11	j.	j.	PROPN
eurjchem-1150	214	12	;	;	PUNCT
eurjchem-1150	214	13	zacchigna	zacchigna	PROPN
eurjchem-1150	214	14	,	,	PUNCT
eurjchem-1150	214	15	m.	m.	NOUN
eurjchem-1150	214	16	;	;	PUNCT
eurjchem-1150	214	17	bonivento	bonivento	NOUN
eurjchem-1150	214	18	,	,	PUNCT
eurjchem-1150	214	19	p.	p.	NOUN
eurjchem-1150	214	20	;	;	PUNCT
eurjchem-1150	214	21	frausin	frausin	PROPN
eurjchem-1150	214	22	,	,	PUNCT
eurjchem-1150	214	23	f.	f.	PROPN
eurjchem-1150	214	24	;	;	PUNCT
eurjchem-1150	214	25	carcia	carcia	PROPN
eurjchem-1150	214	26	,	,	PUNCT
eurjchem-1150	214	27	v.	v.	CCONJ
eurjchem-1150	214	28	eur	eur	PROPN
eurjchem-1150	214	29	.	.	PUNCT
eurjchem-1150	215	1	j.	j.	PROPN
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eurjchem-1150	215	3	.	.	PROPN
eurjchem-1150	215	4	chem	chem	PROPN
eurjchem-1150	215	5	.	.	PUNCT
eurjchem-1150	216	1	2006	2006	NUM
eurjchem-1150	216	2	,	,	PUNCT
eurjchem-1150	216	3	41	41	NUM
eurjchem-1150	216	4	,	,	PUNCT
eurjchem-1150	216	5	192‐200	192‐200	NUM
eurjchem-1150	216	6	.	.	PUNCT
eurjchem-1150	217	1	[	[	X
eurjchem-1150	217	2	6	6	NUM
eurjchem-1150	217	3	]	]	PUNCT
eurjchem-1150	217	4	.	.	PUNCT
eurjchem-1150	218	1	marcos	marcos	PROPN
eurjchem-1150	218	2	,	,	PUNCT
eurjchem-1150	218	3	i.	i.	PROPN
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eurjchem-1150	218	5	;	;	PUNCT
eurjchem-1150	218	6	escola	escola	PROPN
eurjchem-1150	218	7	,	,	PUNCT
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eurjchem-1150	218	9	a.	a.	PROPN
eurjchem-1150	218	10	;	;	PUNCT
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eurjchem-1150	218	12	,	,	PUNCT
eurjchem-1150	218	13	r.	r.	PROPN
eurjchem-1150	218	14	f.	f.	PROPN
eurjchem-1150	218	15	;	;	PUNCT
eurjchem-1150	218	16	basabe	basabe	NOUN
eurjchem-1150	218	17	,	,	PUNCT
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eurjchem-1150	218	19	;	;	PUNCT
eurjchem-1150	218	20	diez	diez	PROPN
eurjchem-1150	218	21	,	,	PUNCT
eurjchem-1150	218	22	d.	d.	PROPN
eurjchem-1150	218	23	;	;	PUNCT
eurjchem-1150	218	24	sanz	sanz	PROPN
eurjchem-1150	218	25	,	,	PUNCT
eurjchem-1150	218	26	f.	f.	PROPN
eurjchem-1150	218	27	;	;	PUNCT
eurjchem-1150	218	28	mollinedo	mollinedo	PROPN
eurjchem-1150	218	29	,	,	PUNCT
eurjchem-1150	218	30	f.	f.	PROPN
eurjchem-1150	218	31	;	;	PUNCT
eurjchem-1150	218	32	dela	dela	PROPN
eurjchem-1150	218	33	iglesia‐vicente	iglesia‐vicente	PROPN
eurjchem-1150	218	34	,	,	PUNCT
eurjchem-1150	218	35	j.	j.	PROPN
eurjchem-1150	218	36	;	;	PUNCT
eurjchem-1150	218	37	sierrac	sierrac	PROPN
eurjchem-1150	218	38	,	,	PUNCT
eurjchem-1150	218	39	b.	b.	PROPN
eurjchem-1150	218	40	g.	g.	PROPN
eurjchem-1150	218	41	;	;	PUNCT
eurjchem-1150	218	42	urones	urones	PROPN
eurjchem-1150	218	43	,	,	PUNCT
eurjchem-1150	218	44	j.	j.	PROPN
eurjchem-1150	218	45	g.	g.	PROPN
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eurjchem-1150	218	47	.	.	PUNCT
eurjchem-1150	219	1	med	med	PROPN
eurjchem-1150	219	2	.	.	PROPN
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eurjchem-1150	219	4	.	.	PUNCT
eurjchem-1150	220	1	2007	2007	NUM
eurjchem-1150	220	2	,	,	PUNCT
eurjchem-1150	220	3	15	15	NUM
eurjchem-1150	220	4	,	,	PUNCT
eurjchem-1150	220	5	5719‐5737	5719‐5737	NUM
eurjchem-1150	220	6	.	.	PUNCT
eurjchem-1150	221	1	perla	perla	PROPN
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eurjchem-1150	221	3	fadnavis	fadnavis	NOUN
eurjchem-1150	221	4	/	/	SYM
eurjchem-1150	221	5	european	european	PROPN
eurjchem-1150	221	6	journal	journal	PROPN
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eurjchem-1150	221	8	chemistry	chemistry	NOUN
eurjchem-1150	221	9	6	6	NUM
eurjchem-1150	221	10	(	(	PUNCT
eurjchem-1150	221	11	1	1	NUM
eurjchem-1150	221	12	)	)	PUNCT
eurjchem-1150	221	13	(	(	PUNCT
eurjchem-1150	221	14	2015	2015	NUM
eurjchem-1150	221	15	)	)	PUNCT
eurjchem-1150	221	16	93‐97	93‐97	NUM
eurjchem-1150	221	17	97	97	NUM
eurjchem-1150	222	1	[	[	X
eurjchem-1150	222	2	7	7	NUM
eurjchem-1150	222	3	]	]	PUNCT
eurjchem-1150	222	4	.	.	PUNCT
eurjchem-1150	223	1	takahashi	takahashi	PROPN
eurjchem-1150	223	2	,	,	PUNCT
eurjchem-1150	223	3	m.	m.	NOUN
eurjchem-1150	223	4	;	;	PUNCT
eurjchem-1150	223	5	dodo	dodo	NOUN
eurjchem-1150	223	6	,	,	PUNCT
eurjchem-1150	223	7	k.	k.	PROPN
eurjchem-1150	223	8	;	;	PUNCT
eurjchem-1150	223	9	sugimoto	sugimoto	PROPN
eurjchem-1150	223	10	,	,	PUNCT
eurjchem-1150	223	11	y.	y.	PROPN
eurjchem-1150	223	12	;	;	PUNCT
eurjchem-1150	223	13	aoyagi	aoyagi	PROPN
eurjchem-1150	223	14	,	,	PUNCT
eurjchem-1150	223	15	y.	y.	PROPN
eurjchem-1150	223	16	;	;	PUNCT
eurjchem-1150	223	17	yamada	yamada	PROPN
eurjchem-1150	223	18	,	,	PUNCT
eurjchem-1150	223	19	y.	y.	PROPN
eurjchem-1150	223	20	;	;	PUNCT
eurjchem-1150	223	21	hashimoto	hashimoto	NOUN
eurjchem-1150	223	22	,	,	PUNCT
eurjchem-1150	223	23	y.	y.	PROPN
eurjchem-1150	223	24	;	;	PUNCT
eurjchem-1150	223	25	shirai	shirai	PROPN
eurjchem-1150	223	26	,	,	PUNCT
eurjchem-1150	223	27	r.	r.	PROPN
eurjchem-1150	223	28	bioorg	bioorg	PROPN
eurjchem-1150	223	29	.	.	PUNCT
eurjchem-1150	224	1	med	med	PROPN
eurjchem-1150	224	2	.	.	PROPN
eurjchem-1150	224	3	chem	chem	PROPN
eurjchem-1150	224	4	.	.	PUNCT
eurjchem-1150	225	1	lett	lett	PROPN
eurjchem-1150	225	2	.	.	PROPN
eurjchem-1150	225	3	2000	2000	NUM
eurjchem-1150	225	4	,	,	PUNCT
eurjchem-1150	225	5	10	10	NUM
eurjchem-1150	225	6	,	,	PUNCT
eurjchem-1150	225	7	2571‐	2571‐	NUM
eurjchem-1150	225	8	2574	2574	NUM
eurjchem-1150	225	9	.	.	PUNCT
eurjchem-1150	226	1	[	[	X
eurjchem-1150	226	2	8	8	NUM
eurjchem-1150	226	3	]	]	PUNCT
eurjchem-1150	226	4	.	.	PUNCT
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eurjchem-1150	226	6	,	,	PUNCT
eurjchem-1150	226	7	d.	d.	PROPN
eurjchem-1150	226	8	;	;	PUNCT
eurjchem-1150	226	9	philippe	philippe	PROPN
eurjchem-1150	226	10	,	,	PUNCT
eurjchem-1150	226	11	n.	n.	NOUN
eurjchem-1150	226	12	;	;	PUNCT
eurjchem-1150	226	13	metzger	metzger	PROPN
eurjchem-1150	226	14	,	,	PUNCT
eurjchem-1150	226	15	s.	s.	PROPN
eurjchem-1150	226	16	;	;	PUNCT
eurjchem-1150	226	17	bhargava	bhargava	PROPN
eurjchem-1150	226	18	,	,	PUNCT
eurjchem-1150	226	19	a.	a.	NOUN
eurjchem-1150	226	20	;	;	PUNCT
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eurjchem-1150	226	22	,	,	PUNCT
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eurjchem-1150	226	24	;	;	PUNCT
eurjchem-1150	226	25	lieb	lieb	PROPN
eurjchem-1150	226	26	,	,	PUNCT
eurjchem-1150	226	27	f.	f.	PROPN
eurjchem-1150	226	28	;	;	PUNCT
eurjchem-1150	226	29	waldmann	waldmann	PROPN
eurjchem-1150	226	30	,	,	PUNCT
eurjchem-1150	226	31	h.	h.	PROPN
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eurjchem-1150	226	34	.	.	PUNCT
eurjchem-1150	227	1	chem	chem	NOUN
eurjchem-1150	227	2	.	.	PUNCT
eurjchem-1150	228	1	soc	soc	PROPN
eurjchem-1150	228	2	.	.	PUNCT
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eurjchem-1150	229	2	,	,	PUNCT
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eurjchem-1150	229	4	,	,	PUNCT
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eurjchem-1150	229	6	.	.	PUNCT
eurjchem-1150	230	1	[	[	X
eurjchem-1150	230	2	9	9	NUM
eurjchem-1150	230	3	]	]	PUNCT
eurjchem-1150	230	4	.	.	PUNCT
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eurjchem-1150	231	5	;	;	PUNCT
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eurjchem-1150	231	7	,	,	PUNCT
eurjchem-1150	231	8	t.	t.	PROPN
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eurjchem-1150	231	10	;	;	PUNCT
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eurjchem-1150	231	13	h.	h.	PROPN
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eurjchem-1150	231	15	;	;	PUNCT
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eurjchem-1150	231	23	q.	q.	PROPN
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eurjchem-1150	231	25	;	;	PUNCT
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eurjchem-1150	232	2	.	.	PUNCT
eurjchem-1150	233	1	res	re	NOUN
eurjchem-1150	233	2	.	.	PUNCT
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eurjchem-1150	234	2	,	,	PUNCT
eurjchem-1150	234	3	29	29	NUM
eurjchem-1150	234	4	,	,	PUNCT
eurjchem-1150	234	5	624‐626	624‐626	PROPN
eurjchem-1150	234	6	.	.	PUNCT
eurjchem-1150	235	1	[	[	X
eurjchem-1150	235	2	10	10	NUM
eurjchem-1150	235	3	]	]	PUNCT
eurjchem-1150	235	4	.	.	PUNCT
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eurjchem-1150	236	2	,	,	PUNCT
eurjchem-1150	236	3	s.	s.	PROPN
eurjchem-1150	236	4	;	;	PUNCT
eurjchem-1150	236	5	shi	shi	PROPN
eurjchem-1150	236	6	,	,	PUNCT
eurjchem-1150	236	7	z.	z.	PROPN
eurjchem-1150	236	8	;	;	PUNCT
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eurjchem-1150	236	10	,	,	PUNCT
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eurjchem-1150	236	12	tetrahedron	tetrahedron	PROPN
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eurjchem-1150	236	14	,	,	PUNCT
eurjchem-1150	236	15	55	55	NUM
eurjchem-1150	236	16	,	,	PUNCT
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eurjchem-1150	236	18	.	.	PUNCT
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eurjchem-1150	237	2	11	11	NUM
eurjchem-1150	237	3	]	]	PUNCT
eurjchem-1150	237	4	.	.	PUNCT
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eurjchem-1150	237	6	,	,	PUNCT
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eurjchem-1150	237	8	;	;	PUNCT
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eurjchem-1150	237	12	;	;	PUNCT
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eurjchem-1150	237	14	,	,	PUNCT
eurjchem-1150	237	15	d.	d.	PROPN
eurjchem-1150	237	16	;	;	PUNCT
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eurjchem-1150	237	18	,	,	PUNCT
eurjchem-1150	237	19	s.	s.	PROPN
eurjchem-1150	237	20	;	;	PUNCT
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eurjchem-1150	238	2	,	,	PUNCT
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eurjchem-1150	238	4	,	,	PUNCT
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eurjchem-1150	239	2	12	12	NUM
eurjchem-1150	239	3	]	]	PUNCT
eurjchem-1150	239	4	.	.	PUNCT
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eurjchem-1150	240	2	,	,	PUNCT
eurjchem-1150	240	3	g.	g.	PROPN
eurjchem-1150	240	4	;	;	PUNCT
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eurjchem-1150	240	7	,	,	PUNCT
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eurjchem-1150	240	9	;	;	PUNCT
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eurjchem-1150	240	13	s.	s.	PROPN
eurjchem-1150	240	14	;	;	PUNCT
eurjchem-1150	240	15	yadav	yadav	PROPN
eurjchem-1150	240	16	,	,	PUNCT
eurjchem-1150	240	17	j.	j.	PROPN
eurjchem-1150	240	18	s.	s.	PROPN
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eurjchem-1150	240	21	,	,	PUNCT
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eurjchem-1150	240	23	,	,	PUNCT
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eurjchem-1150	241	2	13	13	NUM
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eurjchem-1150	241	7	p.	p.	PROPN
eurjchem-1150	241	8	c.	c.	PROPN
eurjchem-1150	241	9	;	;	PUNCT
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eurjchem-1150	241	11	,	,	PUNCT
eurjchem-1150	241	12	r.	r.	PROPN
eurjchem-1150	241	13	h.	h.	PROPN
eurjchem-1150	241	14	;	;	PUNCT
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eurjchem-1150	241	22	k.	k.	PROPN
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eurjchem-1150	241	25	.	.	PUNCT
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eurjchem-1150	242	2	,	,	PUNCT
eurjchem-1150	242	3	22	22	NUM
eurjchem-1150	242	4	,	,	PUNCT
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eurjchem-1150	242	6	.	.	PUNCT
eurjchem-1150	243	1	[	[	X
eurjchem-1150	243	2	14	14	NUM
eurjchem-1150	243	3	]	]	PUNCT
eurjchem-1150	243	4	.	.	PUNCT
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eurjchem-1150	244	5	;	;	PUNCT
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eurjchem-1150	245	2	,	,	PUNCT
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eurjchem-1150	245	4	,	,	PUNCT
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eurjchem-1150	245	6	.	.	PUNCT
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eurjchem-1150	246	2	15	15	NUM
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eurjchem-1150	247	2	,	,	PUNCT
eurjchem-1150	247	3	p.	p.	PROPN
eurjchem-1150	247	4	r.	r.	PROPN
eurjchem-1150	247	5	;	;	PUNCT
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eurjchem-1150	247	7	,	,	PUNCT
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eurjchem-1150	247	12	,	,	PUNCT
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eurjchem-1150	247	14	,	,	PUNCT
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