Synthesis of Alkyl (+/-)-2,3-Di-O-acylglycerates and Attempts Directed to their Conversion into Alkyl (R)-2,3-Di-O-acylglycerates by Enzyme-catalyzed Enantioselective Deacylation Reactions

Article abstract of DOI:10.1002/prac.19933350709

By screening several lipases and proteases as catalysts for an enantioselective partial deacylation of methyl (+/-)-2,3-di-O-acylglycerates, it was found that methyl (R)-2,3-di-butanoylglycerate can be obtained with an enantiomeric excess of >96percent and a yield of 20percent related to the racemic starting material.This was prepared from methyl acrylate through dihydroxylation with potassium permanganate at -30 deg C and a subsequent bisacylation.