An efficient asymmetric synthesis of diacylglycerols

C. Vilcheze, R. Bittman

Research output: Contribution to journalComment/debate

22 Scopus citations

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 languageEnglish (US)
Pages (from-to)734-738
Number of pages5
JournalJournal of Lipid Research
Volume35
Issue number4
Publication statusPublished - Jan 1 1994
Externally publishedYes

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Keywords

  • 1,2-dipalmitoyl-sn-glycerol
  • deprotection of 4- methoxyphenyl group
  • dihydroxylation

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Cell Biology

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