Synthesis and mass spectrometry of 1-acyl and 3-acyl-sn-glycerol carbonates.

sn-Glycerol-1,2-carbonate was prepared fromD-serine,sn-glycerol-2,3-carbonate fromL-serine, via 1-0- or 3-0-benzyl-sn-glycerol, respectively.sn-Glycerol-2,3-carbonate was also prepared fromD-mannitol orD-serine following thesn-glycerol-3-β,β,β-trichloroethylcarbonate route.sn-Glycerol-1,2-carbonate andsn-glycerol-2,3-carbonate were acylated with saturated and unsaturated fatty acid chlorides to form 3-acyl-sn-glycerol-1,2-carbonates and 1-acyl-sn-glycerol-2,3-carbonates, respectively. The mass spectra of the enantiomeric monoacyl-sn-glycerol carbonates showed molecular ions and acyl cations (RCO(+)) of high intensity. The heterocyclic dioxolan-2-one ring was remarkably stable during electron impact.