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% overall yield. The desired phosphocholine was prepared from diacylglycerol (6) by sequential phosporylation by POCl3, reaction with choline p-toluenesulfonate, and aqueous hydrolysis. Purification was accomplished by treatment of crude 1 with ion-exchange resin. Diacylglycerol (6) was prepared by esterification of rac-1-benzyloxy-2,3-propanediol with perfluorinated acid followed by hydrogenolysis of the protective group.