Regio- and Diastereoselective Lipase-Catalyzed Preparation of Acetylated2-O-Glucosylglycerols

Article abstract of DOI:10.1016/0957-4166(94)80181-9

2-O-(β-D-Glucopyranosyl)glycerol and 2-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)glycerol have been submitted to lipase-catalyzed acetylation using Pseudomonas cepacia (LPS) and Candida antarctica (LCA) lipases in organic solvent.The reactions involved the glycerol moiety and were highly diastereoselective: LPS yielded the (2S)-1-O-acetyl-derivative, while, more interestingly, LCA yielded the (2R)-1-O-acetyl-derivative; in this way the natural compound lilioside A could be obtained.Conversely, lipase-catalyzed hydrolysis of the fullyacetylated 1,3-di-O-acetyl-2-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)glycerol using LCA furnished the (2S)-1-O-acetyl-derivative showing the same steric preference as the reverse reaction.