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Generation and Use of Glycosyl Radicals under Acidic Conditions: Glycosyl Sulfinates as Precursors |
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| Authors: | Shiyang Xu Wei Zhang Caiyi Li Yanjing Li Hongxin Zeng Prof Yingwei Wang Yang Zhang Prof Dawen Niu |
| Institution: | 1. Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China
These authors contributed equally to this work.;2. Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041 China;3. Laboratory of Clinical Nuclear Medicine, Department of Nuclear Medicine, West China Hospital of Sichuan University, Chengdu, 610041 China |
| Abstract: | We herein report a method that enables the generation of glycosyl radicals under highly acidic conditions. Key to the success is the design and use of glycosyl sulfinates as radical precursors, which are bench-stable solids and can be readily prepared from commercial starting materials. This development allows the installation of glycosyl units onto pyridine rings directly by the Minisci reaction. We further demonstrate the utility of this method in the late-stage modification of complex drug molecules, including the anticancer agent camptothecin. Experimental studies provide insight into the reaction mechanism. |
| Keywords: | Glycoside Synthesis Glycosyl Radicals Glycosyl Sulfinates Minisci Reaction |