Organic letters

Protecting group free glycosidations using p-toluenesulfonohydrazide donors

AV Gudmundsdottir, M Nitz

Index: Gudmundsdottir, Anna V.; Nitz, Mark Organic Letters, 2008 , vol. 10, # 16 p. 3461 - 3463

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Citation Number: 40

Abstract

N′-Glycopyranosylsulfonohydrazides are introduced as glycosyl donors for protecting group free synthesis of O-glycosides, glycosyl azides, and oxazolines. Mono-and disaccharides containing a reducing terminal N-acetylglucosamine residue were condensed with p-toluenesulfonylhydrazide to give the desired β-d-pyranose donors. These donors can be activated with NBS and then glycosidated with the desired alcohol or transformed to ...