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 [1]

Abstract

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