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Facile and stereo-controlled synthesis of 2-deoxynojirimycin, Miglustat and Miglitol |
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| Authors: | Zhen-Xing ZhangBaolin Wu Bin WangTie-Hai Li Peng-Fei ZhangLi-Na Guo Wen-jun WangWei Zhao Peng George Wang |
| Affiliation: | a College of pharmacy, Nankai University, Tianjin 300071, China b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China c Departments of Chemistry and Biochemistry, The Ohio State University, Columbus, OH 43210, USA |
| Abstract: | A novel and facile synthesis of a series of the biologically significant iminosugar derivatives including 2-deoxynojirimycin, Miglustat and Miglitol is reported. The synthesis features a strategic double inversion mechanism for securing the desired stereochemistry at C5 position of such glucose-type carbohydrate mimetics, representing a practical and remarkable improvement on the previously reported method that suffers from the loss of the stereo-control during the reaction process. |
| Keywords: | DNJ Miglustat Miglitol Mitsunobu reaction Double inversion strategy |
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