Citation: Yan Nan, Lei Zhi-Wei, Su Jia-Kun, Liao Wei-Lin, Hu Xiang-Guo. Ring opening of sugar-derived epoxides by TBAF/KHF₂: An attractive alternative for the introduction of fluorine into the carbohydrate scaffold[J]. Chinese Chemical Letters, ;2017, 28(2): 467-470. doi: 10.1016/j.cclet.2016.10.006 shu

Ring opening of sugar-derived epoxides by TBAF/KHF₂: An attractive alternative for the introduction of fluorine into the carbohydrate scaffold

Yan Nan ^a ,
Lei Zhi-Wei ^a ,
Su Jia-Kun ^b ,
Liao Wei-Lin ^a,, ,
Hu Xiang-Guo ^a,,

a.
National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China
b.
Center of R & D, China Tobacco Jiangxi Industrial Co., Ltd., Nanchang 330096, China

Corresponding author: Liao Wei-Lin, lmmtmmt@gmail.com Hu Xiang-Guo, huxiangg@iccas.ac.cn
Received Date: 17 June 2016
Revised Date: 12 September 2016
Accepted Date: 23 September 2016
Available Online: 13 February 2016

Figures(3)

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-thioglycosides can be ring-opened to afford fluorinated carbohydrate products in high yields and in short reaction times.
- Carbohydrate,
- Fluorinated carbohydrate,
- Fluoro-sugar,
- Organofluorine,
- Epoxide
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Ring opening of sugar-derived epoxides by TBAF/KHF2: An attractive alternative for the introduction of fluorine into the carbohydrate scaffold

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通讯作者: 陈斌, bchen63@163.com

Ring opening of sugar-derived epoxides by TBAF/KHF₂: An attractive alternative for the introduction of fluorine into the carbohydrate scaffold