3 years ago

Stereoselective Epimerizations of Glycosyl Thiols

Stereoselective Epimerizations of Glycosyl Thiols
Patrick McArdle, Lisa M. Doyle, Paul V. Murphy, Claudia Di Salvo, Michelle McKinney, Shane O’Sullivan
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02760

DOI: 10.1021/acs.orglett.7b02760

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