A. Hermetter, Herbert Stütz, R. Franzmair
Apr 1, 1989
Citations
0
Influential Citations
35
Citations
Journal
Chemistry and Physics of Lipids
Abstract
Abstract Reaction of the sn-glycero-3-phosphocholine zinc chloride complex with tritylchloride yields 1-O-tritylglycerophosphocholine, which can be used as the starting material for a convenient two-step synthesis of mixed-acid 1,2-diacyl-sn-glycero-3-phosphocholines. Acylation of tritylglycerophosphocholine by conventional procedures gives 1-O-trityl-2-acyl-sn-glycerophosphocholine. Then, in a one-pot reaction with fatty acid anhydrides or acyltriazolides in the presence of borontrifluoride-etherate as a catalyst, the trityl group of tritylacylglycerophosphocholine is replaced by an acyl moiety. The final product is obtained in excellent yield (75–90%) and high isomeric purity (97–99%). The procedure described can be carried out with milligram quantities as well as on a technical scale.