18330-40-0Relevant academic research and scientific papers
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.
