A General Method for the Synthesis of Glycerophospholipids and Their Analogues via H-Phosphonate Intermediates

Article abstract of DOI:10.1021/jo00267a020

A general chemical method for the synthesis of glycerophospholipids and their analogues via H-phosphonate intermediates has been developed.It was found that 1,2-dipalmitoylglycero-3-H-phosphonate, prepared by the reaction of 1,2-dipalmitoylglycerol with PCl3/imidazole, reacts with various hydroxylic components (choline tosylate, N-(tert-butoxycarbonyl)ethanolamine, N-(tert-butoxycarbonyl)-L-serine) in the presence of condensing agents to produce in high yield the corresponding glycero-3-H-phosphonate diesters.These can be converted into natural phospholipids via oxidation with iodine or into thio or seleno analogues by using sulfur or selenium as oxidant, respectively.