Synthesis of glycosyl phosphoramidates: Novel isosteric analogues of glycosyl phosphates

Several newer isosteric analogues of glycosyl phosphates, namely of glycosyl phosphoramidates, were synthesized in good yields using Staudinger reaction of their corresponding azides with trimethyl phosphite followed by de-O-acetylation. The structure and conformation of the fully protected analogue synthesized, namely 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl bismethoxyphosphoramidate, was established by X-ray crystallography. © 2001 Elsevier Science Ltd. All rights reserved.