The synthesis of chiral glycerides starting from D- and L-serine

Chem Phys Lipids. 1976 Mar;16(2):115-22. doi: 10.1016/0009-3084(76)90003-7.

Abstract

A method for synthesizing chiral glycerides starting from L- or D-serine is described. Optically-active serine (both enantiomers are commerically available) was transformed into glyceric acid by stereospecific diazotization. The configuration at carbon atom 2 was maintained during the reaction. The glyceric acid was then converted into optically pure isopropylideneglycerol - which is an important intermediate in the synthesis of mono-, di- and triglyderides - by esterification followed by acetalization with acetone and reduction with lithium aluminium hydride. Reaction of this intermediate with triphenylphosphine in tetrachloromethane followed by acid-catalysed hydrolysis and dehydrohalogenation provided optically-active glycidol (2,3-epoxy-1-propanol). The epoxy ring of an ester of glycidol and a fatty acid was then opened stereospecifically with retention of configuration by heating the glycidol ester in the presence of a second fatty acid and a catalyst. This yielded a chiral 1,3-diglyceride which could be converted into a chiral triglyceride.

MeSH terms

  • Diglycerides / chemical synthesis
  • Glycerides / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Methods
  • Molecular Conformation
  • Optical Rotation
  • Serine
  • Stereoisomerism
  • Structure-Activity Relationship
  • Triglycerides / chemical synthesis

Substances

  • Diglycerides
  • Glycerides
  • Triglycerides
  • Serine