Stereoselective epimerizations of glycosyl thiols
Doyle, Lisa M. ; O'Sullivan, Shane ; Di Salvo, Claudia ; McKinney, Michelle ; McArdle, Patrick ; Murphy, Paul V.
Doyle, Lisa M.
O'Sullivan, Shane
Di Salvo, Claudia
McKinney, Michelle
McArdle, Patrick
Murphy, Paul V.
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2017-10-17
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Article
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Doyle, Lisa M., O’Sullivan, Shane, Di Salvo, Claudia, McKinney, Michelle, McArdle, Patrick, & Murphy, Paul V. (2017). Stereoselective Epimerizations of Glycosyl Thiols. Organic Letters, 19(21), 5802-5805. doi: 10.1021/acs.orglett.7b02760
Abstract
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 β-d-manno- and β-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.
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American Chemical Society
Publisher DOI
10.1021/acs.orglett.7b02760
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Attribution-NonCommercial-NoDerivs 3.0 Ireland