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

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...

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Bibliographic Details
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
Description
Summary: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.

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