Reactions of Azides of Sugars with Derivatives of Tri-Valent Phosphorus Leading to N-Phosphorylated Sugars

This communication deals with a simple method for preparation of X-phosphorylated sugars by the reaction of trivalent phosphorus derivatives with 1-α,β-azides of 2,3,4,5-tetraacetylated and 2,3,4,6-tetra(trimethyl)silylated glycose. It has been established that ohosphimine derivatives, obtained as a result of the Staudinger reaction, can be easily hydrolyzed to give derivatives of acetylated glucosaminphosphoric acids. It has been discovered that susceptibility to hydrolysis depends on the phosphorus suhstituents. When using esters of trivalent phosphorus the rate of hydrolysis for compounds with alkyl substituents decreases in order C 3 H 7 > C 2 H 5 O >> CH 3 O This can probably be explained by the electronic and steric influence of the alkyl groups.