Factors Affecting Stereocontrol during Glycosidation of 2,3-Oxazolidinone-Protected 1-Tolylthio-<i>N</i>-acetyl-<scp>d</scp>-glucosamine

Abstract

[reaction: see text] It is demonstrated that a ring-fused 2,3-oxazolidinone-protected derivative of 1-tolylthio-N-acetyl-D-glucosamine undergoes high-yield glycosidation under mild donor activation conditions. Stereoselective formation of alpha-linked or beta-linked glycosides is dependent on reactivity of acceptor alcohols, where rate of glycosidation correlates to stereochemical outcome. Evidence for the role of glycosyl triflate intermediates and the N-acetyl substituent of the 2N,3O-oxazolidinone ring in stereochemical control is presented.