Synthesis of enantiomeric mixed-acid α,β-diglycerides

A procedure has been developed that permits the synthesis of mixed-acid α,β-diglycerides in either one of the four theoretically possible isomeric forms. Each is obtainable as a pure compound devoid of any contamination with positional or spatial isomers. Their fatty acid substituents may consist either of two dissimilar saturated fatty acids or a saturated and an unsaturated fatty acid. The procedure has been applied to the synthesis of d-α-stearoyl-β-oleoylglycerol and d-α-oleoyl-β-stearoylglycerol, the first mixed-acid diglycerides to be obtained in enantiomeric form.