Isosteres of natural phosphates. 5. The preparation of phosphotidycholine, phosphotidylethanolamine and phosphotidylglycerol.

ABSTRACT

Isosteric phosphonate analogues of phosphatidylcholine, phosphatidylethanolamine and phosphatidylglycerol have been prepared in which the normal oxygen atom of the phosphate ester linkage in the glycerol backbone of the molecule has been replaced by a methylene group. These have been prepared by the coupling of the previously reported phosphotidic acid (isosteric analogue of phosphatidic acid) with the appropriate protected hydroxyl compound mediated by trichloroacetonitrile. In all cases, racemic materials have been isolated for the analogue of phosphatidylglycerol, a mixture of two enantiomeric pairs is isolated.