The lipase-catalyzed acylation of 1,2-O-isopropylidene glycerol was studied. The products obtained were hydrolyzed to their corresponding 1-monostearoylglycerides. Different approaches were investigated, and for the transesterification of ethyl stearate with (rac)-1,2-O-isopropylidene glycerol 1 in various organic solvents the highest initial rates were found in n-heptane and n-dodecane. The direct esterification of 1 with stearic acid gave the highest conversion (84%). Variation of the alkyl residue of stearate led to a decrease in the initial rates in the order : ethyl --> methyl approximate to propyl --> butylstearate. An enantioselective reaction was found for the faster reacting R-enantiomer in the transesterification of 1 with ethyl stearate resulting in 11%ee for the product. To elucidate the reasons for the low stereoselectivity, reactions of R- and S-1,2-O-isopropylidene glycerol with ethyl stearate in n-heptane were carried out. The remaining activity of the lipase was between 50 and 85% after 50 to 600 h reaction time.