83526-72-1Relevant articles and documents
Synthesis of glyceryletherphosphatides, 1st communication. Preparation of 1-0-octadecyl-2-0-acetyl-sn-glyceryl-3-phosphorylcholine ('platelet activating factor'), of its enantiomer and of some analogous compounds
Hirth,Barner
, p. 1059 - 1084 (1982)
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Lipase-catalysed kinetic resolution of 1-O-alkylglycerols by sequential transesterification
Halldorsson, Arnar,Thordarson, Pall,Kristinsson, Bjorn,Magnusson, Carlos D.,Haraldsson, Gudmundur G.
, p. 2893 - 2899 (2007/10/03)
The natural S-configured chimyl, batyl and selachyl alcohols of the 1-O-alkylglycerol type were prepared by enantioselective lipase-catalysed transesterification. Their racemates were synthesised in two steps by reacting racemic solketal with the bromides of the corresponding fatty alcohols and a subsequent conversion of the intermediates into the 1-O-alkylglycerols by deprotection under acidic aqueous conditions. The Pseudomonas fluorescens lipase was employed to kinetically resolve the racemic 1-O-alkylglycerols by a sequential diacetylation process to afford them virtually enantiomerically pure. Dramatic enantioselectivity increase was observed for the saturated chimyl (E = 17-32) and batyl (E = 14-38) alcohols at decreased temperature, whereas for the monounsaturated selachyl (E = 12-13) alcohol no such temperature effects were observed.