PHOSPHONOLIPIDS: XI. SYNTHESIS OF PHOSPHONOLIPID METABOLITES. L-α-GLYCERYL-(2-TRIMETHYLAMMONIUMETHYL)PHOSPHONATE

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Abstract
The synthesis of a possible intermediate in phosphonolipid metabolism, viz. L-[alpha]-glyceryl-(2-trimethylammoniumethyl) phosphonate, a phosphonic acid analogue of L-[alpha]-glycerylphosphoryl-choline, is described. The compound was obtained by condensation of D-acetone glycerol with (2-bromoethyl) metaphosphonate in boiling benzene, removal of the acetone group of the condensation product by acid hydrolysis, treatment of the hydrolysis product in dimethyl-formamide with trimethylamine at 60-62[degree] for 3 days, isolation of L-[alpha]-glyceryl)-(2-trimethylammoniumethyl)phosphate as cardmium chloride complex. Removal of the cadmium chloride was effected with a mixture of Amberlites IR-45 and IRC-50. A procedure for the preparation of (2-bromoethyl)metaphosphonate is reported.