Organic Letters 2008-08-21

Protecting group free glycosidations using p-toluenesulfonohydrazide donors.

Anna V Gudmundsdottir, Mark Nitz

Index: Org. Lett. 10(16) , 3461-3, (2008)

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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 beta- d-pyranose donors. These donors can be activated with NBS and then glycosidated with the desired alcohol or transformed to the oxazoline or glycosyl azide.