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-beta-D-glucopyranosyl bismethoxyphosphoramidate, was established by X-ray crystallography.
Kannan
T
T
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India.
Vinodhkumar
S
S
Varghese
B
B
Loganathan
D
D
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
C448387:2,3,4,6-tetra-O-acetyl-glucopyranosyl bismethoxyphosphoramidate; D009005:Monosaccharides