Synthesis of thiophosphoramidates in water: Click chemistry for phosphates

摘要

An aqueous method for the preparation of N,S-dialkyl thiophosphoramidates is reported. Thiophosphorylation of alkylamines was performed using SPCI3 in aqueous reaction media, and the resulting thiophosphoramidate-S-anions were S-alkylated with soft electrophiles. Ranges of amines and electrophiles were explored. Phosphate esters and their structural analogues represent a major class of biomolecules that plays central roles in genetic transmission, membrane formation, signalling and metabolism. The synthesis of phosphate esters and their analogues has been revolutionized by the phosphoramidite method.1 However, the