SYNTHESIS AND HYDROLYTIC BEHAVIOR OF RAC- 1-ALKYL-2-ACYLGLYCERO-3-PHOSPHODICHLORIDES

1-Hexadecyl-2-palmitoylglycero-3-phosphodichloride was quntitatively o btained in the reaction of an appropriate glycerol derivative with an excess phosphoryl chloride in the presence of amine at 0-3 degrees C, and its structure was confirmed at low temperature H-1, C-13, and P-31 NMR. The substance proved to be stable ina chloroform solution at 0-3 degrees C and, thus, useful for preparative syntheses. At room temper ature in the acidic medium, it was revealed that the compound prepared undergoes hydrolytic degradation, which includes the splitting of a p hosphodiester bond, the migration of its 2-acyl group to the position 3 in the glycerol backbone, and chlorination. At 0-3 degrees C, its ba sic hydrolysis (e.g., in the presence of triethyamine or KHCO3) result ed in the formation of the corresponding salts of phosphatidic acid.