Organic letters

Facile approach to 2-acetamido-2-deoxy-β-D-glucopyranosides via a furanosyl oxazoline

Y Cai, CC Ling, DR Bundle

Index: Cai, Ye; Ling, Chang-Chun; Bundle, David R. Organic Letters, 2005 , vol. 7, # 18 p. 4021 - 4024

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Citation Number: 51

Abstract

A concise and convenient route that may be easily scaled is reported for the preparation of unprotected β-glucopyranosides of N-acetyl-d-glucosamine. Reaction of a wide variety of alcohols with a reactive, readily prepared furanosyl oxazoline under acidic conditions affords the corresponding β-d-glucopyranosides in good to high yields. Primary alcohols gave only β-d-glucopyranosides. A mechanism is proposed for this transformation.