Preparation of phospholipid analogues using the phosphoramidite route

Abstract

The phosphoramidite route has been used to prepare phospholipid analogues possessing biocompatible properties and the monomer 2-(methacryloyloxy)ethylphosphorylcholine, utilised in the preparation of biocompatible polymers. Modifications to established methodology include, as an alternative to the thermally unstable tetrazole, the use of 4,5-dichloroimidazole as an acid catalyst for preparing phosphite esters from the corresponding phosphoramidites, and the use of trimethylamine N-oxide as oxidant for the conversion of the phosphite esters into the corresponding phosphates.