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Issue 30, 2012
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Chemoselective Staudinger-phosphite reaction of symmetrical glycosyl-phosphites with azido-peptides and polygycerols

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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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Article information


Submitted
27 Jan 2012
Accepted
18 May 2012
First published
12 Jun 2012

Org. Biomol. Chem., 2012,10, 6211-6216
Article type
Paper

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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