166734-75-4Relevant academic research and scientific papers
Total synthesis of (+)- and (-)-ononitol
Pietrusiewicz,Salamonczyk
, p. 1863 - 1867 (1995)
A practical, five-step synthetic sequence for conversion of myo-inositol into enantiomerically pure (+)- and (-)-ononitols in 17% and 18% overall yield, respectively, has been developed.
Lipase Regioselective O-Acetylations of a myo-Inositol Derivative: Efficient Desymmetrization of 1,3-Di-O-benzyl-myo-inositol
Ribeiro, Marcela F. P.,Pais, Karla C.,de Jesus, Barbara S. M.,Fernandez-Lafuente, Roberto,Freire, Denise M. G.,Manoel, Evelin A.,Simas, Alessandro B. C.
, p. 386 - 391 (2018/01/27)
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.
Sulfonate protecting groups. Synthesis of O- and C-methylated inositols: D- and L-ononitol, D- and L-laminitol, mytilitol and scyllo-inositol methyl ether
Sarmah, Manash P.,Shashidhar, Mysore S.,Sureshan, Kana M.,Gonnade, Rajesh G.,Bhadbhade, Mohan M.
, p. 4437 - 4446 (2007/10/03)
Syntheses of d- and l-ononitol, d- and l-laminitol, mytilitol and scyllo-inositol methyl ether starting from myo-inositol are described. One or two of the myo-inositol 1,3,5-orthoformate hydroxyl groups were protected as tosylates. These mono or ditosylat
