PMID-sentid	Pub_year	Sent_text		comp_official_name	comp_offsetprotein_name	organism	prot_offset
1445679-4	1992	The epoxide O atom is syn to the tetrahydrofuran O atom.	Epoxy Compounds	4-11	synemin	Homo sapiens	22-25	
3731388-8	1986	Two major in vivo products were shown to derive from 3MC alcohols, particularly 3-hydroxymethyl-cholanthrene, and probably involved both syn and anti-diol-epoxide metabolites.	Epoxy Compounds	155-162	synemin	Homo sapiens	137-140	
24599150-1	2014	The salen Co(III)-catalyzed phenolic kinetic resolution of racemic anti- or syn-azido and benzyloxy epoxides provides a practical route to a range of enantioenriched anti- or syn-1-aryloxy-3-azido or benzyloxy-2-alcohols in excellent yields and ees.	Epoxy Compounds	100-108	synemin	Homo sapiens	76-79	
3891118-2	1985	From these calculations on tetrahydroepoxides, one infers that substitution of a methyl group in the same bay-region as the epoxide should destabilize both syn-diaxial and anti-diequatorial bay-region diol-epoxide diastereomers with respect to the syn-diequatorial and anti-diaxial diastereomers.	Epoxy Compounds	37-44	synemin	Homo sapiens	156-159	
3891118-2	1985	From these calculations on tetrahydroepoxides, one infers that substitution of a methyl group in the same bay-region as the epoxide should destabilize both syn-diaxial and anti-diequatorial bay-region diol-epoxide diastereomers with respect to the syn-diequatorial and anti-diaxial diastereomers.	Epoxy Compounds	37-44	synemin	Homo sapiens	248-251	
3891118-3	1985	The results of these calculations, together with recent experimental observations, suggest that the enhanced in vivo binding to DNA of the isomer having the methyl group and the epoxide in the same bay-region (1,2-diol-3,4-epoxide of 5-MeC) might be partially due to this destabilization of the syn-diaxial diastereomer.	Epoxy Compounds	178-185	synemin	Homo sapiens	295-298	
33427829-2	2021	Herein, we successively consider their Upjohn"s syn dihydroxylation and their anti-dihydroxylation via an epoxidation reaction followed by epoxide opening reaction.	Epoxy Compounds	139-146	synemin	Homo sapiens	48-51	
26587719-2	2015	Here we describe how an umpolung strategy that involves the addition of Grignard reagents to alpha-epoxy N-sulfonyl hydrazones-directed by the alkoxide of the 1-azo-3-alkoxy propenes formed in situ via base-induced ring opening of the epoxide-leads to the syn-selective production of alpha-alkyl-beta-hydroxy N-sulfonyl hydrazones with alpha-quaternary centres.	Epoxy Compounds	235-242	synemin	Homo sapiens	256-259	
22897831-0	2012	syn-beta-Hydroxyallylic silanes from terminal epoxide alpha-lithiation-silylation and alkenylation: application to the tetrahydrofuran portion of the lytophilippines.	Epoxy Compounds	46-53	synemin	Homo sapiens	0-3	
22963654-7	2012	Moreover, we have experimentally demonstrated that the rearrangement is stereoconvergent, a feature that is traced back to the initial configuration of the epoxide, which determines the somewhat counterthermodynamic placement of the metal syn to the methyl group of the stereogenic center in the 2H-pyran intermediate.	Epoxy Compounds	156-163	synemin	Homo sapiens	239-242	
22897831-1	2012	Lithiation-in situ silylation of terminal epoxides using lithium 2,2,6,6-tetramethylpiperidide in combination with phenyldimethyl(or diethyl)silyl chloride provides a direct process for the synthesis of trans-alpha,beta-epoxysilanes, which undergo alpha-ring opening with alkenylcoppers to give syn-beta-hydroxyallylic silanes.	Epoxy Compounds	42-50	synemin	Homo sapiens	190-193	
20509635-1	2010	A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF(3) x OEt(2) in CH(2)Cl(2) at -20 degrees C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective S(N)1-type epoxide ring-opening process.	Epoxy Compounds	28-35	synemin	Homo sapiens	192-195	
22315965-1	2012	A concise and highly stereoselective total synthesis of manzacidin B and its congeners has been developed following chelation-controlled syn-epoxidation and Lewis acid catalyzed intramolecular regioselective epoxide ring opening to generate the quarternary amine center.	Epoxy Compounds	208-215	synemin	Homo sapiens	43-46	
21194209-1	2011	A highly regio- and stereoselective synthesis of novel beta,gamma-disubstituted gamma-lactams with either an anti or syn relative configuration was developed from readily available epoxide and aziridine acetates.	Epoxy Compounds	181-188	synemin	Homo sapiens	36-39	
15653329-3	2005	The intramolecular reaction occurred exclusively through the anti-epoxide to provide the 5,5-cis-fused bicycle, whereas the syn-epoxide, which theoretically would provide the 5,5-trans-fused bicycle, remained unchanged.	Epoxy Compounds	128-135	synemin	Homo sapiens	124-127	
19642691-2	2009	Functionalization of a range of allylic 3-(N,N-dibenzylamino)cycloalk-1-enes with m-CPBA in the presence of Cl(3)CCO(2)H gives exclusively the corresponding syn-epoxide for the 5-membered ring (>99:1 dr), the anti-epoxide for the 8-membered ring (>99:1 dr), and predominantly the anti-epoxide for the 7-membered ring (94:6 dr).	Epoxy Compounds	161-168	synemin	Homo sapiens	157-160	
19642691-2	2009	Functionalization of a range of allylic 3-(N,N-dibenzylamino)cycloalk-1-enes with m-CPBA in the presence of Cl(3)CCO(2)H gives exclusively the corresponding syn-epoxide for the 5-membered ring (>99:1 dr), the anti-epoxide for the 8-membered ring (>99:1 dr), and predominantly the anti-epoxide for the 7-membered ring (94:6 dr).	Epoxy Compounds	217-224	synemin	Homo sapiens	157-160	
17567130-2	2007	Syn and anti methylation of epoxides 8, 9, 14, and 16 enables access to all eight possible diastereomeric stereotetrads, seven of which are commonly found in polypropionate natural products.	Epoxy Compounds	28-36	synemin	Homo sapiens	0-3	
16438527-0	2006	Anti versus syn opening of epoxides derived from 9-(3-deoxy-beta-D-glycero-pent-3-enofuranosyl)adenine with Me3Al: factors controlling the stereoselectivity.	Epoxy Compounds	27-35	synemin	Homo sapiens	12-15	
15756325-0	2005	Mild metal-free syn-stereoselective ring opening of activated epoxides and aziridines with aryl borates.	Epoxy Compounds	62-70	synemin	Homo sapiens	16-19	
19236033-2	2009	The iterative epoxide-based methodology consists of the syn-selective epoxidation of cis homoallylic alcohols with use of the VO(acac)(2)-catalyzed conditions followed by epoxide cleavage with a propynyl aluminum reagent as key steps.	Epoxy Compounds	14-21	synemin	Homo sapiens	56-59	
19236033-2	2009	The iterative epoxide-based methodology consists of the syn-selective epoxidation of cis homoallylic alcohols with use of the VO(acac)(2)-catalyzed conditions followed by epoxide cleavage with a propynyl aluminum reagent as key steps.	Epoxy Compounds	171-178	synemin	Homo sapiens	56-59	
18774860-1	2008	A practical and enantioselective total synthesis of hyacinthacine A1 is achieved involving syn allylic epoxide opening with retention using Pd catalysis and "domino" hydrogenation (five steps in one pot) sequences.	Epoxy Compounds	103-110	synemin	Homo sapiens	39-42	
16438527-3	2006	It was found that the stereoselectivity of epoxide ring opening (anti versus syn) varied significantly upon changing the amount of Me3Al, the solvent, the O-silyl protecting group, and the reaction temperature.	Epoxy Compounds	43-50	synemin	Homo sapiens	77-80	
15548057-1	2004	The presence of an alkenyl substituent on the terminal epoxide of a polyepoxide substrate enhances the yield of all-endo-regioselective tandem oxacyclization to trans-syn-trans-fused polycyclic ethers.	Epoxy Compounds	55-62	synemin	Homo sapiens	167-170	
8625498-6	1996	It was found that the syn-DB[a,l]P diolepoxide-14-N7Ade adduct is formed via trans addition to the epoxide.	Epoxy Compounds	39-46	synemin	Homo sapiens	22-25	
15281167-3	2004	Since the stereochemistry of the trans-fused 6,7-ring system is determined by the epoxide, the method also allows the construction of trans-syn 6,7-ring systems.	Epoxy Compounds	82-89	synemin	Homo sapiens	140-143	
10810705-2	2000	The stereochemical outcome, anti or syn, is achieved by the Lewis acid-mediated ring expansion of stereochemically homogeneous epoxides in a reaction related to the pinacol rearrangement.	Epoxy Compounds	127-135	synemin	Homo sapiens	36-39	
15496102-1	2004	[reaction: see text] Smooth and selective Payne rearrangement was achieved for the above types of epoxyalcohols with a CF(3) group so as to form thermodynamically more stable alkoxides, where the strongly electron-withdrawing nature of this moiety played a significantly important role and was proved to overcome increased steric instability of epoxides from syn-E to anti-Z isomers.	Epoxy Compounds	345-353	synemin	Homo sapiens	359-362