Abstract
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.
Original language | English (US) |
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Pages (from-to) | 734-738 |
Number of pages | 5 |
Journal | Journal of Lipid Research |
Volume | 35 |
Issue number | 4 |
State | Published - 1994 |
Externally published | Yes |
Keywords
- 1,2-dipalmitoyl-sn-glycerol
- deprotection of 4- methoxyphenyl group
- dihydroxylation
ASJC Scopus subject areas
- Biochemistry
- Endocrinology
- Cell Biology