Radical Dehydroxymethylative Fluorination of Carbohydrates and Divergent Transformations of the Resulting Reverse Glycosyl Fluorides
文献类型： 外文期刊
作者： Zhou, Xin 1 ; Ding, Han 1 ; Chen, Pengwei 1 ; Liu, Li 1 ; Sun, Qikai 1 ; Wang, Xianyang 1 ; Wang, Peng 1 ; Lv, Zhihua 1 ; Li 1 ;
作者机构： 1.Ocean Univ China, Chinese Minist Educ, Key Lab Marine Med, Sch Med & Pharm, 5 Yushan Rd, Qingdao 266003, Peoples R China
2.Qingdao Natl Lab Marine Sci & Technol, Lab Marine Drugs & Bioprod, Qingdao 266237, Peoples R China
3.Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Hainan Key Lab Res & Dev Nat Prod Li Folk Med, Haikou 571101, Hainan, Peoples R China
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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