Chemical synthesis of a polymerizable bis-substituted phosphoethanolamine

Abstract The first chemical synthesis of a 1,2-bis-substituted polymerizable-sn-glycerol-3-phosphoethanolamine is reported. The synthetic approach utilizes the preparation of 1,2-bis(16-methy 1-2,4-(E,E)-octadecadienoyl)-3-(4-methoxybenzyl)-sn-glycerol via the acylation of 3-(4-methoxybenzyl)-sn-glycerol with 16-methyl-2,4-(E,E)-octadecadienoic acid. The deprotection of the 4-methoxybenzyl ether group is accomplished in high yield via Lewis acid catalyzed hydrolysis at −78°C. The final step is the phosphorylation of this 1,2-bis(dienoyl)-sn-glycerol.