Chemoselective Staudinger-phosphite reaction of symmetrical glycosyl-phosphites with azido-peptides and polygycerolsThis article is part of the Organic & Biomolecular Chemistry 10th Anniversary issue.Electronic supplementary information (ESI) available: Synthetic protocols for the synthesis of glycosyl-phosphites, Staudinger-phosphite reactions with peptides and PG, SPR measurements, characterization of the synthesised compounds. See DOI: 10.1039/c2ob25207d

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. In this paper we present the synthesis of glyco-phosphoramidate conjugates as easily accessible analogs of glyco-phosphorous esters via the Staudinger-phosphite reaction.