Muraoka Takahiro, Adachi Kota, Chowdhury Rainy, Kinbara Kazushi
Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Aoba-ku, Sendai, Japan; PRESTO, Japan Science and Technology Agency, Kawaguchi, Saitama, Japan.
Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Aoba-ku, Sendai, Japan.
PLoS One. 2014 Mar 24;9(3):e91912. doi: 10.1371/journal.pone.0091912. eCollection 2014.
Transetherification on polyols involving intra- and intermolecular nucleophilic substitutions is reported. Di- or trialkoxide formation of propane-1,3-diol or 2-(hydroxymethyl)propane-1,3-diol derivatives by NaH triggers the reaction via oxetanes formation, where the order to add NaH and a polyol significantly influences the yields of products. It was demonstrated that the protective group on the pentaerythritol skeleton is apparently transferred to the hydrophilic and hydrophobic chain molecules bearing a leaving group in one-step, and a protective group conversion from tosyl to benzyl was successful using a benzyl-appending triol to afford a desired product in 67% yield.
报道了涉及分子内和分子间亲核取代的多元醇的酯交换反应。通过NaH形成1,3 - 丙二醇或2 - (羟甲基)-1,3 - 丙二醇衍生物的二烷氧基或三烷氧基，通过氧杂环丁烷的形成引发反应，其中添加NaH和多元醇的顺序对产物收率有显著影响。结果表明，季戊四醇骨架上的保护基团明显一步转移到带有离去基团的亲水性和疏水性链分子上，并且使用带有苄基的三醇成功实现了从甲苯磺酰基到苄基的保护基团转化，以67%的收率得到所需产物。
