Carbohydrate research

Syntheses of the 3-and 4-thio analogues of 4-nitrophenyl 2-acetamido-2-deoxy-β-d-gluco-and galactopyranoside

HM Chen, SG Withers

Index: Chen, Hong-Ming; Withers, Stephen G. Carbohydrate Research, 2007 , vol. 342, # 15 p. 2212 - 2222

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Citation Number: 13

Abstract

The syntheses of 4-nitrophenyl β-glycosides of the 3-thio and 4-thio analogues of the two principal 2-acetamido-2-deoxy-hexoses found in living systems, GlcNAc and GalNAc, are described. While synthesis of the 4-thio analogues could be achieved via nucleophilic displacements of sulfonate derivatives with thioacetate, problems with neighbouring group acetamido participation necessitated the use of sulfamidate intermediates for the 3-thio ...