Tetrahedron: Asymmetry

Thio-sugars. Part 5: From d-glucal to 3-deoxy-(1→ 2)-2-S-thiodisaccharides through isolevoglucosenone—a simple approach

ZJ Witczak, H Chen, P Kaplon

Index: Witczak, Zbigniew J.; Chen, Hong; Kaplon, Peter Tetrahedron Asymmetry, 2000 , vol. 11, # 2 p. 519 - 532

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Citation Number: 25

Abstract

A new synthesis of isolevoglucosenone and its stereoselective functionalization into 3-deoxy- (1-2)-2-S-thiodisaccharides is described. The base-catalyzed conjugate addition of 1- thiosugars to isolevoglucosenone followed by the reduction of the C-4 keto function constitute a new two-step general approach to these classes of biologically important thio- sugars.

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