3-H-2,1-benzoxathiol-3-one 1-oxide - A new reagent for stereospecific oxidation of nucleoside H-phosphonothioate diesters

Article abstract of DOI:10.1016/S0040-4039(00)79848-0

Oxidation of diastereomerically pure nucleoside H-phosphonothioate diesters with 3-H-2,1-benzoxathiol-3-one 1-oxide (1) was found to be stereospecific and occurred with retention of configuration. Absolute configurations of diribonucleoside H-phosphonothioate diastereomers were established via stereochemical correlation using m-chloroperoxybenzoic acid for stereospecific conversion of ribonucleoside H-phosphonothioate to the corresponding H-phosphonate diesters.