SYNTHESIS OF ENANTIOMERIC MIXED-ACID GLYCEROLPHOSPHATIDES: I.L-α-(α′-STEAROYL,β-OLEOYL)CEPHALIN ANDL-α-(α′-OLEOYL,β-STEAROYL)CEPHALIN

Abstract

α′-Stearoyl,β-oleoyl L-α-glycerylphosphorylethanolamine and α′-oleoyl,β-stearoyl L-α-glycerylphosphorylethanolamine were synthesized by phosphorylating D-α′-stearoyl,β-oleoylglycerol and D-α′-oleoyl,β-stearoylglycerol with phosphorus oxychloride and quinoline, esterifying the resulting mixed-acid phosphatidic acid dichlorides with 2′-hydroxyethylphthalimide in the presence of pyridine, and removing the protective phthaloyl group of the α′-stearoyl,β-oleoyl-, and α′-oleoyl,β-stearoyl-L-α-glycerylphosphoryl-2′-hydroxyethylphthalimides by hydrazinolysis.