Regio- and Diastereoselective Lipase-catalyzed Preparation of Acetylated 2-O-glucosylglycerols

• Published in: Tetrahedron: Asymmetry
• Main Authors: D. COLOMBO, F. RONCHETTI, A. SCALA, I. M. TAINO, F. M. ALBINI, TOMA, LUCIO
• Other Authors: D., Colombo, F., Ronchetti, A., Scala, I. M., Taino, F. M., Albini, Toma, Lucio
• Format: Article in Journal/Newspaper
• Language: English
• Published: 1994
• Subjects: Antarc*; Antarctica
• Online Access: http://hdl.handle.net/11571/453820; https://doi.org/10.1016/0957-4166(94)80181-9

2-O-(beta-D-Glucopyranosyl) glycerol and 2-O-(2',3',4',6'-tetra-O-acetyl-beta-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-acetylderivative, 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 fully acetylated 1,3-di-O-acetyl-2-O-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)gl ycerol using LCA furnished the (2S)-1-O-acetyl-derivative showing the same steric preference as the reverse reaction.