An efficient and scalable synthesis of perfluorinated phosphatidylcholines

Perfluorinated glycerophosphocholine (1), which is useful as an emulsifier in fluorocarbon suspensions, was prepared in multikilogram scale in 38% ove rall yield. The desired phosphocholine was prepared from diacylglycerol (6) by sequential phosporylation by POCl3, reaction with choline p-toluene-sul fonate, and aqueous hydrolysis, Purification was accomplished by treatment of crude I with ion-exchange resin. Diacylglycerol (6) was prepared by este rification of rac-1-benzyloxy-2,3-propanediol with perfluorinated acid foll owed by hydrogenolysis of the protective group.