Efficient kinetic resolution of (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol with the lipase B of Candida antarctica

(±)-1,2-O-Isopropylidene-3,6-di-O-benzyl-myo-inositol is a relevant starting material in the synthesis of inositol phosphates and their analogs. In this study, we disclose our efforts toward an efficient methodology for the kinetic resolution of this compound by lipase B of Candida antarctica (Novoz...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2010-12, Vol.21 (24), p.2899-2903
Main Authors: Cunha, Aline G., da Silva, Angelo A.T., da Silva, Antônio J.R., Tinoco, Luzineide W., Almeida, Rodrigo V., de Alencastro, Ricardo B., Simas, Alessandro B.C., Freire, Denise M.G.
Format: Article
Language:English
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Summary:(±)-1,2-O-Isopropylidene-3,6-di-O-benzyl-myo-inositol is a relevant starting material in the synthesis of inositol phosphates and their analogs. In this study, we disclose our efforts toward an efficient methodology for the kinetic resolution of this compound by lipase B of Candida antarctica (Novozym 435). This reaction selectively affords L-(−)-1,2-O-isopropylidene-5-O-acetyl-3,6-di-O-benzyl-myo-inositol. From a conversion of 34% with EtOAc as an acylating agent, the use of vinyl acetate increased the yield to over 49%, while maintaining a very high ee (>99%). The combination of the latter reagent with TBME as a solvent accelerates the reaction.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2010.12.006