Regioselectiveα-Phosphorylation of Aldoses in Aqueous Solution

Abstract

Amidotriphosphate and diamidophosphate are reagents for the regioselective α-phosphorylation of aldoses. The mechanism involves the carbonyl addition product (see scheme); the hydroxy groups are phosphorylated by an intramolecular phosphate group transfer with formation of a cyclic intermediate, which is then hydrolyzed to the O-phosphorylated product.