Preparative synthesis of 1,2-and 1,3-disubstituted phosphatidic acids

A general preparative method for the synthesis of 1,2(3)-diacyl and 1-alkyl -2(3)-acyl phosphatidic acids by examples with acyl = COC15H31 and alkyl = C16H33 was proposed. The procedure involved two stages: the in teraction of 1,2- or 1,3-disubstituted glycerols with POCl3 at 0-3 degrees C leading to the corresponding phosphodichlorides, and their hydrolysis with 80% aqueou s DMSO or DMF at room temperature, The corresponding phosphatidic acids wer e isolated in the form of pyridinium salts in approximately 80% yields. In the absence of DMSO or DMF, the hydrolysis of 1-hexadecyl-2-palmitoyl 3-gly cerophosphodichloride with aqueous pyridine resulted in an admixture of P,P '-bis(1-hexadecyl-2-palmitoyl)-3-glyceryl pyrophosphate (10-30 mol %) along with the corresponding phosphatidic acid. This admixture also gave the tar get phosphatidic acid upon hydrolysis in aqueous DMSO.