Issue 30, 2012

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

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

Supplementary files

Article information

Article type
Paper
Submitted
27 ጃንዩ 2012
Accepted
18 ሜይ 2012
First published
12 ጁን 2012

Org. Biomol. Chem., 2012,10, 6211-6216

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

V. Böhrsch, T. Mathew, M. Zieringer, M. R. J. Vallée, L. M. Artner, J. Dernedde, R. Haag and C. P. R. Hackenberger, Org. Biomol. Chem., 2012, 10, 6211 DOI: 10.1039/C2OB25207D

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