Peer-Reviewed Journal Details
Mandatory Fields
Doyle, LM;O'Sullivan, S;Di Salvo, C;McKinney, M;McArdle, P;Murphy, PV
2017
November
Organic Letters
Stereoselective Epimerizations of Glycosyl Thiols
Published
Optional Fields
GLUCURONIC-ACID GLYCOSIDATION REACTIONS OLIGOSACCHARIDE ANOMERIZATION GLYCOCONJUGATION THIOGLYCOSIDES REACTIVITY SUGARS SNCL4
19
5802
5805
Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective beta-D-manno- and beta-L-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.
1523-7060
10.1021/acs.orglett.7b02760
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