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.
- 相关文献
作者其他论文 更多>>
-
Genome-Enabled Analyses Reveal Roles of Mangrove Homeobox Superfamily in Response to Salinity
作者：Chen, Tingting;Chen, Tingting;Ye, Xiuxu;Wang, Peng;Feng, Erhui;Zhang, Yu;Wang, Peng
关键词：Homeobox superfamily; Rhizophoraceae; Mangrove; Salinity stress
-
Identification of targets and comparative study of administration methods for the lipid-lowering effects of fucoidan from Saccharina japonica
作者：Chen, Pengwei;Wang, Hao;Chen, Huiqin;Dai, Haofu;Hao, Li;Li, Quancai;Zhang, Miao;Jiang, Hongfei;Zhang, Renshuai;Jia, Ang
关键词：Fucoidan; Lipid-lowering activity; Dietary supplementation; Intestinal target; Gut microbiota
-
Monitoring of yellow leaf disease (YLD) damage based on ground-based LiDAR and UAV multispectral data
作者：Zhang, Xudong;Bi, Peiyun;Zhou, Quan;Ren, Lili;Luo, Youqing;Liu, Li
关键词：LiDAR; Multispectral imaging; Data fusion; Classification of damage; Machine learning
-
On the Study of Joint YOLOv5-DeepSort Detection and Tracking Algorithm for Rhynchophorus ferrugineus
作者：Wu, Shuai;Wang, Jianping;Chen, Danyang;Lu, Huimin;Wu, Shuai;Wei, Wei;Ji, Xiangchuan;Yang, Bin;Liu, Li
关键词：Red Palm Weevil; YOLOv5; joint YOLOv5-DeepSort; target tracking
-
Cashew nut oligopeptide inhibits mast cell degranulation by suppressing activation of the NF-Κb signalling pathway
作者：Chen, Di;Zhou, Xin;Chen, Jian;Chen, Di;Zhou, Xin;Chen, Jian;Chen, Di;Zhang, Yan
关键词：Cashew nut protein; Oligopeptides; Degranulation; Mast cell; NF-kappa B signalling pathway
-
PbrSYP71 regulates pollen tube growth by maintaining polar distribution of the endoplasmic reticulum in Pyrus
作者：Zhang, Mingliang;Tang, Chao;Wang, Zhiqi;Lan, Chi;Yue, Dong;Zhang, Ningyi;Xie, Zhihua;Qian, Ming;Sun, Mengjun;Liu, Zongqi;Xie, Zhu;Zhang, Hao;Zhang, Shaoling;Wang, Peng;Wu, Juyou;Zhang, Mingliang;Liu, Zhuqin;Wu, Juyou
关键词：endoplasmic reticulum; F-actin; PbrSYP71; pear (
Pyrus bretschneideri ); pollen tube; syntaxin -
Gapless genome assembly and population genomics highlights diversity of mango germplasms
作者：Zhang, Cuixian;Bai, Tianqi;Luo, Qiong;Zhang, Cuixian;Yi, Huaifeng;Xie, Dehong;Bai, Tianqi;Ni, Zhangguang;Luo, Xinping;Lok, Yusuf Chong Yu;Ye, Xiuxu;Fu, Jingxiao;Gong, Xinyue;Wang, Peng;Lok, Yusuf Chong Yu
关键词：
