Radical Dehydroxymethylative Fluorination of Carbohydrates and Divergent Transformations of the Resulting Reverse Glycosyl Fluorides

文献类型： 外文期刊

第一作者： Zhou, Xin

作者： Zhou, Xin;Ding, Han;Chen, Pengwei;Liu, Li;Sun, Qikai;Wang, Xianyang;Wang, Peng;Lv, Zhihua;Li, Ming;Lv, Zhihua;Li, Ming;Chen, Pengwei

作者机构：

关键词： alkoxyl radicals; carbohydrates; C-F bond activation; fluorination; radical reactions

期刊名称：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION （ 影响因子：15.336； 五年影响因子：14.205 ）

ISSN： 1433-7851

年卷期： 2020 年 59 卷 10 期

页码：

收录情况： SCI

摘要： A mild and convenient method for the synthesis of reverse glycosyl fluorides (RGFs) has been developed that is based on the silver-promoted radical dehydroxymethylative fluorination of carbohydrates. A salient feature of the reaction is that furanoid and pyranoid carbohydrates furnish structurally diverse RGFs bearing a wide variety of functional groups in good to excellent yields. Intramolecular hydrogen atom transfer experiments revealed that the reaction involves an underexploited radical fluorination that proceeds via beta-fragmentation of sugar-derived primary alkoxyl radicals. Structurally divergent RGFs were obtained by catalytic C-F bond activation, and our method thus offers a concise and efficient strategy for the synthesis of reverse glycosides by late-stage diversification of RGFs. The potential of this method is showcased by the preparation and diversification of sotagliflozin, leading to the discovery of a promising SGLT2 inhibitor candidate.

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