Selective Monoprotection of Symmetrical Diols in a Flow Reactor  

作　　者：Hisashi Masui Masaru Takizawa Yuki Sakai Yasuhiro Kajiwara Kiyofumi Wanibuchi Mitsuru Shoji Takashi Takahashi 

机构地区：[1]Department of Pharmaceutical Sciences, Yokohama University of Pharmacy, Yokohama, Japan

出　　处：《International Journal of Organic Chemistry》2018年第2期264-271,共8页有机化学国际期刊（英文）

摘　　要：Desymmetrization reactions provide a powerful approach for the construction of complex molecules. Various methods have been developed for the selective monoprotection of symmetrical diols;however, their application to large-scale operations is limited. In this study, the monotetrahydropyranylation of symmetrical diols in a flow reactor has been developed, whereby the length of the flow reactor tube and the amount of acid were optimized. A higher selectivity for the monoprotected derivative was observed when the reaction was performed in a flow reactor compared with that observed in a conventional batch experiment. The efficient flow method developed herein can be applied to large-scale synthesis by numbering up the flow reactor without affecting the selectivity and yield. Since monoprotection can be achieved without using a large excess of diol, our developed flow method is effective when expensive diol must be used.Desymmetrization reactions provide a powerful approach for the construction of complex molecules. Various methods have been developed for the selective monoprotection of symmetrical diols;however, their application to large-scale operations is limited. In this study, the monotetrahydropyranylation of symmetrical diols in a flow reactor has been developed, whereby the length of the flow reactor tube and the amount of acid were optimized. A higher selectivity for the monoprotected derivative was observed when the reaction was performed in a flow reactor compared with that observed in a conventional batch experiment. The efficient flow method developed herein can be applied to large-scale synthesis by numbering up the flow reactor without affecting the selectivity and yield. Since monoprotection can be achieved without using a large excess of diol, our developed flow method is effective when expensive diol must be used.

关 键 词：DESYMMETRIZATION SELECTIVE Monoprotection FLOW Synthesis DIOLS TETRAHYDROPYRANYLATION 

分 类 号：O6[理学—化学]