Short-route Synthesis of a Glycerophospholipid Bearing an Unsaturated Acyl Group at the sn-1 Position

Abstract

A short-route synthesis of an optically active phosphocholine bearing an unsaturated acyl group at the sn-1 position was developed via lipase-catalyzed enantioselective acylation of 2-O-methoxyeth-oxymethylglycerol, removal of the MEM group by employing cat-echol boron bromide, subsequent DCC-mediated acylation of the hydroxy group at the 2-position and final introduction of a choline phosphate moiety.