Preparation of Optically Active 1-O-Alkyl-3-O-arylsulfonyl-sn-glycerol Derivatives: Substrate Engineering in Enzyme-Mediated Enantioselective Hydrolysis

Lipase PS catalyzes the enantioselective hydrolysis of various 2-acetyl compounds of the 1-O-alkyl-3-O-arylsulfonyl-sn-glycerol derivatives to afford the corresponding optically active compounds. Changing the structure of the 1-O-alkyl and 3-O-arylsulfortyl groups affects both the reactivity and enantioselectivity. Finally, the E value of the reaction for 2-acetyl-3-O-3,5-dimethyl-benzenesulfonyl-1-O-4-methoxybenzyl-sn-glycerol is greater than 200.