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Factors Affecting Stereocontrol during Glycosidation of 2,3-Oxazolidinone-Protected 1-Tolylthio-N-acetyl-d-glucosamine

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Peng Wei and Robert J. Kerns*

Division of Medicinal & Natural Product Chemistry, University of Iowa, Iowa City, Iowa 52242-1112 robert-kerns@uiowa.edu

J. Org. Chem., 2005, 70 (10), pp 4195–4198

DOI: 10.1021/jo047812o

Publication Date (Web): April 13, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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.

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Published In Issue May 13, 2005
Received December 14, 2004

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Factors Affecting Stereocontrol during Glycosidation of 2,3-Oxazolidinone-Protected 1-Tolylthio-N-acetyl-d-glucosamine

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

N-Benzyl-2,3-oxazolidinone as a Glycosyl Donor for Selective α-Glycosylation and One-Pot Oligosaccharide Synthesis Involving 1,2-cis-Glycosylation

Oxazolidinone Protected 2-Amino-2-deoxy-d-glucose Derivatives as Versatile Intermediates in Stereoselective Oligosaccharide Synthesis and the Formation of α-Linked Glycosides

Oxazolidinone Protection of N-Acetylglucosamine Confers High Reactivity on the 4-Hydroxy Group in Glycosylation

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