Studies on reactions of nucleoside H-phosphonates with bifunctional reagents. Part 1. Reaction with amino alcohols

Abstract

The reaction of nucleoside H-phosphonates with amino alcohols in the presence of condensing agents has been studied. Depending on the coupling procedure used and the length of the polymethylene bridge in the amino alcohols, different H-phosphonate diesters, cyclic phosphoramidite derivatives or phosphite triesters can be produced. Oxidation of these species with iodine under various experimental conditions has been studied and a general procedure for synthesis of nucleoside alkyl phosphodiesters has been developed.