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

肌醇是一种很有前途的生物质材料。为实现这一目标，需要在肌醇的六个羟基中选择性地取代所需的羟基。这一直是最困难的问题，但是我们已经发现，肌醇在LiCl-二甲基乙酰胺或二甲亚砜中的溶解成功地促进了取代反应，从而根据亲电试剂的量分别产生区域选择性的1，3-二-O-或1-O-取代产物。利用脂肪酶对1，3-二乙酰肌醇进行去对称化，得到了高光学纯度（96%ee）的单乙酸酯。这些基础性研究结果为我们设计合成一种表面活性剂和功能性聚合物单体提供了依据，为肌醇作为生物质的利用奠定了基础。

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.