The Synthesis of Some N-Linked Phospholipid Analogues via Phosphorodiamidate Heterocyclic Intermediates

Novel N-linked phospholipid analogues have been prepared in high yield via heterocyclic phosphorodiamidate intermediates. Thus, 2-chloro-1-methyl-1,3,2-oxazaphosphacyclopentane 2-oxide was prepared from N-methylethanolamine and was allowed to react with a series of (long chain) primary or secondary amines to give cyclic phosphorodiamidate intermediates which could be ring opened using either methanol or ethanol under acidic conditions. In the case of secondary amines alternative routes to the intermediates were sought and, in some cases, gave preferable yields. All intermediates and products were fully characterised by high field multinuclear (¹H, ¹³C, ³¹P) NMR and mass spectrometry and they may display useful physical and biochemical properties.

Novel N-linked phospholipid analogues have been prepared in high yield via heterocyclic phosphorodiamidate intermediates.