Factors affecting stereocontrol during glycosidation of 2,3-oxazolidinone-protected 1-tolylthio-N-acetyl-D-glucosamine.
[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.
Wei
Peng
P
Division of Medicinal & Natural Product Chemistry, University of Iowa, Iowa City, Iowa 52242-1112, USA.
Kerns
Robert J
RJ
D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D006001:Glycoconjugates / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism
C503013:1-tolylthio-N-acetyl-D-glucosamine; D006001:Glycoconjugates; D006027:Glycosides; D023303:Oxazolidinones; D005944:Glucosamine