Preparation of novel N-substituted phospholipids via phosphoramidite intermediates

Abstract

Novel N-alkylated phospholipids have been prepared in high yield by a three-step procedure utilising phosphoramidite intermediates. 3-tert-Butyl-2-chloro-1,3,2-oxazaphosphacyclopentane 1 reacts with alcohols to give cyclic phosphoramidites in near-quantitative yield. These are oxidised to the corresponding phosphates in very high yield with N₂O₄. The phosphates are hydrolysed in water at ambient temperature, via exclusive P–N cleavage, to yield the target phospholipids. Spectral data on the intermediates and products are included and discussed.