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Chemoselective Staudinger-phosphite reaction of symmetrical glycosyl-phosphites with azido-peptides and polygycerols†‡
Thresen Mathew,Maximilian Zieringer,M. Robert J. Vallée,Lukas M. Artner,Jens Dernedde,Rainer Haag,Christian P. R. Hackenberger
Organic & Biomolecular Chemistry Pub Date : 06/12/2012 00:00:00 , DOI:10.1039/C2OB25207D
Abstract

In this paper we present the synthesis of glyco-phosphoramidate conjugates as easily accessible analogs of glyco-phosphorous esters via the Staudinger-phosphite reaction. This protocol takes advantage of synthetically accessible symmetrical carbohydrate phosphites in good overall yields, in which ethylene or propylene linkers can be introduced between phosphorous and galactose or lactose moieties. The phosphites were finally applied for the chemoselective reaction with azido-peptides and polyazido(poly)glycerols.

Graphical abstract: Chemoselective Staudinger-phosphite reaction of symmetrical glycosyl-phosphites with azido-peptides and polygycerols
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