Synthesis of glycosyl phosphoramidates: novel isosteric analogues of glycosyl phosphates

Bioorg Med Chem Lett. 2001 Sep 17;11(18):2433-5. doi: 10.1016/s0960-894x(01)00469-3.

Abstract

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-beta-D-glucopyranosyl bismethoxyphosphoramidate, was established by X-ray crystallography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biochemistry / methods*
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure
  • Monosaccharides / chemical synthesis*
  • Monosaccharides / chemistry

Substances

  • 2,3,4,6-tetra-O-acetyl-glucopyranosyl bismethoxyphosphoramidate
  • Monosaccharides