Studies on Coenzyme Analogs. IV. Sytheses and Properties of β-D-Glucose 1-Phosphoramidate

Abstract

β-D-Glucose 1-phosphoramidate was synthesized by the reaction of silver benzyl phosphoramidate and acetobromoglucose, and successive hydrogenation and deacetylation. The structure of (VII) was confirmed by acid hydrolysis and optical rotation. The amidate had no ability to form pyrophosphate by phosphorolysis with another phosphate, as the other phosphoramidates do, but afforded the β-D-glucose 1, 2-cyclic phosphate, due to the specific configuration which was favorable to intramolecular cyclization. Some discussion was made about this cyclization.