Factors Affecting Stereocontrol during Glycosidation of 2,3-Oxazolidinone-Protected 1-Tolylthio-N-acetyl-d-glucosamine
- 13 April 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (10) , 4195-4198
- https://doi.org/10.1021/jo047812o
Abstract
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 α-linked or β-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.Keywords
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