P. Sonnet
May 1, 1991
Citations
0
Influential Citations
28
Citations
Journal
Chemistry and Physics of Lipids
Abstract
Abstract Glycidyl esters reacted with carboxylic anhydrides in the presence of LiBr in tetrahydrofuran (THF) or benzene to produce 3-bromo-1,2-propanediol esters with no significant acyl migration. Displacement of Br by cesium carboxylates was accomplished cleanly in THF-hexamethylphosphoric triamide (THF-HMPT) at 50–55°C (5 h) completing a highly regioselective triglyceride synthesis. The regioselectivity of these reactions allows stereoselective synthesis if one initiates the short sequence with enantiomerically pure glycidol. Commercial (R)-(+)-glycidol (94.6% R) was used to synthesize (R)- and (S)-lauroyl oleoyl palmitoyl glycerol. 1H-NMR data of S-methoxy-α-trifluoromethylphenyl acetic acid ((S)-MTPA) derivatives formed by reaction of the (S)-MTPA ester of (R)-glycidol indicated that these reactions preserved configuration as expected.