TY - JOUR
T1 - Lipase-catalysed kinetic resolution of 1-O-alkylglycerols by sequential transesterification
AU - Halldorsson, Arnar
AU - Thordarson, Pall
AU - Kristinsson, Bjorn
AU - Magnusson, Carlos D.
AU - Haraldsson, Gudmundur G.
N1 - Funding Information: The University of Iceland Research Fund is acknowledged for financial support, Dr. Sigridur Jonsdottir at the Science Institute for running the NMR analysis, Dr. Sigurdur V. Smarason at deCode Genetics for performing the mass spectrometry analysis, and Svana Stefansdottir at the University of Iceland for elemental analysis.
PY - 2004/9/20
Y1 - 2004/9/20
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/4644275873
U2 - 10.1016/j.tetasy.2004.07.046
DO - 10.1016/j.tetasy.2004.07.046
M3 - Article
SN - 0957-4166
VL - 15
SP - 2893
EP - 2899
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 18
ER -