Methyl 4-toluenesulfonyloxymethylphosphonate, a new and versatile reagent for the convenient synthesis of phosphonate-containing compounds

摘要

A straightforward procedure leading to the new phosphonylating reagent, methyl 4-toluene-sulfonyloxymethylphosphonate, requiring no chromatographic purification is described. This stable reagent works with the same efficiency as dimethyl and other dialkyl esters for the introduction of an O-phosphonomethyl moiety while, in contrast to dimethyl ester, it does not cause any unwanted meth-ylation of sensitive functionalities. Its utility for the alkylation of protected nucleosides in high yield is exemplified.