A synthetic methodology for selective substitution of inositol without protection and its use for preparation of useful functional materials

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Myo-inositol is a promising material as a biomass. To realize this subject, a regioselective substitution on a desired OH group among six ones in inositol should be developed. It has been the most difficult problem, but we have found that dissolution of inositol in LiCl-dimethylacetamide or dimethylsulfoxide successfully promotes a substitution reaction to yield a regioselective 1,3-di-O- or 1-O-substitution product respectively depending on a amount of an electrophile. Desymmetrization of 1,3-diacetyl-myo-inositol by lipase produced monoacetate in a good yield with high optical purity (96% ee).These fundamental research results directed us to design and synthesize a candidate of a surfactant and a monomer for a functional polymer, aiming at the use of myo-inositol as a biomass.