Ring opening of sugar-derived epoxides by TBAF/KHF<sub>2sub>: An attractive alternative for the introduction of fluorine into the carbohydrate scaffold

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• 作者：Nan Yan<sup>asup> ; Zhi-Wei Lei<sup>asup> ; Jia-Kun Su<sup>bsup> ; Wei-Lin Liao<sup>asup><sup> ; sup><sup>lmmtmmt@gmail.comsup> ; Xiang-Guo Hu<sup>asup><sup> ; sup><sup>huxiangg@iccas.ac.cnsup>
• 关键词：Carbohydrate ; Fluorinated carbohydrate ; Fluoro-sugar ; Organofluorine ; Epoxide
• 刊名：Chinese Chemical Letters
• 出版年：2017
• 出版时间：February 2017
• 年：2017
• 卷：28
• 期：2
• 页码：467-470
• 全文大小：597 K
• 卷排序：28

文摘

A stable and commercially available reagent mixture, composed of tetrabutylammonium bifluoride/potassium bifluoride (TBAF/KHF2), was found to be effective for the nucleophilic ring opening reactions of sugar-derived epoxides with fluoride. Different sugar-derived epoxide precursors, including 1-thio-glycosides can be ring-opened to afford fluorinated carbohydrate products in high yields and in short reaction times.