Silver di-t-butyl phosphate, a useful reagent in the synthesis of phospholipids. Synthesis of mixed-acid phosphatidic acid and phosphatidyl glycerolphosphate

Abstract

The synthesis of silver di-t-butyl phosphate is described. Using this reagent, mixed-acid phosphatidic acid with one unsaturated fatty acid could be prepared by means of a reaction with a 1,2-diacyl glycerol-3-iodohydrin. The blocking groups could be removed easily with dry hydrogen chloride at low temperatures. Phosphatidyl glycerolphosphate was prepared by means of a double condensation reaction between 1,3-diiodo-2-t-butyl glycerol and the silver salts of 1,2-diacyl glycerol-3-(benzyl)phosphate and of di-t-butyl phosphate. The protecting groups were released by anionic debenzylation and treatment with hydrogen chloride. Some properties and enzymic degradations of the synthesized compounds are discussed.