CHIROSPECIFIC SYNTHESES OF H-2-LABELED AND C-13-LABELED 1-O-ALKYL-2-O-ALKYL'-SN-GLYCERO-3-PHOSPHOETHANOLAMINES AND 1-O-ALKYL-2-O-ALKYL'-SN-GLYCERO-3-PHOSPHOCHOLINES

A convenient sequence for the synthesis of 1-O-alkyl-2-O-alkyl′-sn-glycero-3-phospholipids was demonstrated starting from 2,3-O-isopropylidene-sn-glycerol, which was first alkylated with 1-bromohexadecane, then converted to the corresponding benzylidene analog. Other less convenient methods to prepare 2,3-O-benzylidene-1-O-hexadecyl-sn-glycerol were also investigated. The key step in the synthesis was the reduction of 2,3-O-benzylidene-1-O-hexadecyl-sn-glycerol with lithium aluminum hydride-aluminum chloride to give 3-O-benzyl-1-O-hexadecyl-sn-glycerol as the major product in 79% yield. The syntheses of 1-O-hexadecyl-2-O-hexadecyl-(1′,1′-d2,-sn-glycero-3-phosphoethanolamine and 1-O-hexadecyl-2-O-hexadecyl-(1′-13C)-sn-glycero-3-phosphoethanolamine as well as the correspondingly labeled sn-glycero-3-phosphocholine analogs were then performed. The optical purites of the synthetic intermediates and the ether lipids were established by a novel 1H-NMR method. © 1990.