Stereoselective Synthesis of S-Linked 2-Deoxy Sugars

Abstract

Stereoselective synthesis of S-linked 2-deoxysugars, potentially nonhydrolyzable mimics of naturally occurring O-linked 2-deoxy sugars, remains a challenge due to the absence of a directing group at C2. This article describes recent efforts in the stereo­selective synthesis of S-linked 2-deoxy sugars, including our approach which involves sulfenylation of stereochemically defined 2-deoxyglycosyl lithiums with asymmetric sugar-derived disulfides.

Key words

2-deoxy sugars - glycosyl lithium - glycosylation - thioglycosides - umpolung

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