The synthesis by phosphoramidite methodology of novel phospholipids related to ethylenediamine

Abstract

Novel phospholipid analogues related to ethylenediamine have been prepared by a rapid three-step procedure. The diazaphosphacyclopentane (1) reacts with alcohols to yield cyclic phosphoramidites in high yield. These are oxidised to the phosphates with N₂O₄. The phosphates undergo a single P–N cleavage under conditions of acid catalysis to yield phospholipid analogues, similar in phosphate structure to natural phospholipids, but with a single substitution of N for O. Full spectroscopic and analytical data are presented and discussed.