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
