Synthesis of DL-alpha-tocopherol-ligated phospholipids

A three-step synthesis of DL-alpha-tocopheryl-6-O-phosphorylcholine and its -6-O-phosphorylethanolamine homologue is described. The reaction pathway involves the conversion of DL-alpha-tocopherol to the corresponding 2-bromoethyl phosphate, hydrolytic cleavage of the remaining phosphorochloridate bond and treatment of the diester intermediate formed with either aqueous trimethylamine or ammonia to give the aminated target derivatives in good overall yields (61-67%). The compounds represent new models of ligated lipid mediators in which a vitamin E-unit is covalently bonded to a naturally occurring phospholipid fragment.