Immunochemical Studies of Phospholipids. II. Syntheses of Cardiolipin and Its Analogues

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Bis (dipalmitoyl D, L-α-glycerylphosphoryl)-1, 3-glycerol disodium salt (I) was synthesized by the condensation of the silver salt of dipalmitoyl D, L-α-glycerophosphoric acid benzyl ester (XI) with 1, 3-diiodopropanol benzyl ether, followed by debenzylation with sodium iodide and hydrogenolysis with palladium black. Bis (dipalmitoyl D, L-α-glycerylphosphoryl)-1, 5-pentanediol disodium salt (III), bis (dipalmitoyl D, L-α-glycerylphosphoryl)-1, 4-butanediol disodium salt (IV), bis (dipalmitoyl D, L-α-glycerylphosphoryl)-1, 2-ethanediol disodium salt (VI) and bis (dipalmitoyl D, L-α-glycerylphosphoryl) methanediol disodium salt (VII) were synthesized similarly by the condensation of the silver salt (XI) with alkyl diiodide or dibromide, followed by debenzylation with sodium iodide. Bis (benzylphosphoryl)-1, 3-propanediol disodium (X) was synthesized by condensation of silver dibenzyl phosphate with alkyl diiodide, followed by debenzylation with sodium iodide.