title: Synthesis of glycosyl phosphoramidates: novel isosteric analogues of glycosyl phosphates.
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.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India.
authors.forename: T
authors.initials: T
authors.lastname: Kannan
authors.forename: S
authors.initials: S
authors.lastname: Vinodhkumar
authors.forename: B
authors.initials: B
authors.lastname: Varghese
authors.forename: D
authors.initials: D
authors.lastname: Loganathan
mesh_terms: D001671:Biochemistry / Q000379:methods*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C448387:2,3,4,6-tetra-O-acetyl-glucopyranosyl bismethoxyphosphoramidate; D009005:Monosaccharides