Carbohydrate research

A highly concise preparation of O-deacetylated arylthioglycosides of N-acetyl-d-glucosamine from 2-acetamido-3, 4, 6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl …

KA Stubbs, MS Macauley, DJ Vocadlo

Index: Stubbs, Keith A.; Macauley, Matthew S.; Vocadlo, David J. Carbohydrate Research, 2006 , vol. 341, # 10 p. 1764 - 1769

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Citation Number: 4

Abstract

An expedient and mild route to a range of aryl 2-acetamido-2-deoxy-1-thio-β-d- glucopyranosides has been devised from 2-acetamido-3, 4, 6-tri-O-acetyl-2-deoxy-α-d- glucopyranosyl chloride and arylthiols or aryl disulfides using phase transfer catalysis conditions. This simple procedure compresses up to three synthetic steps into a one-pot reaction, obviating the need for tedious workups and chromatography and directly ...