Authors: Ribeiro, MFP; Pais, KC; de Jesus, BSM; Fernandez-Lafuente, R; Freire, DMG; Manoel, EA; Simas, ABC

Eur. J. Org. Chem.. vol: . page: 1434-193X.
Date: JAN 23. 2018.
Doi: 10.1002/ejoc.201701417.

Chiral myo-inositol derivatives play key roles in cell-signaling processes. Despite the relevance of these compounds, few syntheses of them rely on enantioselective catalytic reactions. Even fewer reports describe the use of desymmetrization of myo-inositol derivatives. In fact, most routes involve resolution by derivatization. Thus, a symmetrical partially protected myo-inositol derivative, 1,3-di-O-benzyl-myo-inositol (1), was used as a substrate in fast lipase-catalyzed desymmetrization reactions. Among the lipases tested, both Lipozyme RM-IM and Lipozyme TL-IM were effective in catalyzing the formation of the chiral acetate l-(+)-6-O-acetyl-1,3-di-O-benzyl-myo-inositol [l-(+)-2] with high conversion (98-99%) and ee (>99%). Conversely, Novozyme 435 and Lipomod 34P as biocatalysts showed different regioselectivity, leading to the formation of the symmetrical 5-O-acetylated product. We were able to reuse TL-IM lipase seven times without any noticeable decrease in the conversion. Acetate l-(+)-2 is a potential precursor of biologically active myo-inositol derivatives and other relevant materials for cell biology studies..