Journal of Lipid Research, Vol 35, 734-738, Copyright © 1994 by Lipid Research, Inc.
An efficient asymmetric synthesis of diacylglycerols
C Vilcheze and R Bittman
Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing 11367-1597.
A convenient preparation of 1,2-diacyl-sn-glycerol or 2,3-diacyl-sn-
glycerol is described starting from allyl bromide. The latter was converted
to allyl 4-methoxyphenyl ether, which is dihydroxylated using AD-mix as a
catalyst to yield 3-O-(4'-methoxyphenyl)-sn-glycerol or 1-O-
(4'-methoxyphenyl)-sn-glycerol in high yield and high optical purity. After
diacylation, ceric ammonium nitrate was used to remove the 4- methoxyphenyl
group under mild conditions that avoid acyl migration to
1,3-dipalmitoylglycerol. Thus chiral 1,2-diacylglycerol can be prepared
from allyl bromide in just four steps in 78% overall yield and high
enantiomeric excess. This scheme represents an inexpensive method for the
large-scale preparation of chiral 1,2-diacyl-sn-glycerol and 2,3-
diacyl-sn-glycerol.
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