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CuI/TMEDA催化合成芳基葡萄糖碳苷化合物
引用本文:毛泽伟,饶高雄.CuI/TMEDA催化合成芳基葡萄糖碳苷化合物[J].合成化学,2016,24(3):250-252.
作者姓名:毛泽伟  饶高雄
作者单位:云南中医学院 中药学院,云南 昆明 650500
基金项目:云南省应用基础研究计划项目(2014FZ087)
摘    要:以THF为溶剂, CuI/TMEDA为催化剂,四乙酰溴代葡萄糖与芳基溴化镁经取代反应合成了芳基葡萄糖碳苷(2a~2c),其结构经1H NMR和13C NMR确证。该方法立体选择性较好。在最佳反应条件(THF为溶剂,10% CuI和10% TMEDA为催化剂,于0 ℃反应至终点)下,2a~2c的收率为58%~71%, α/β为1/6.5~1/7.1。

关 键 词:CuI  催化  芳基碳苷  合成  
收稿时间:2015-04-17

Synthesis of C-aryl Glycosides Catalyzed by CuI/TMEDA
MAO Ze-wei,RAO Gao-xiong.Synthesis of C-aryl Glycosides Catalyzed by CuI/TMEDA[J].Chinese Journal of Synthetic Chemistry,2016,24(3):250-252.
Authors:MAO Ze-wei  RAO Gao-xiong
Institution:School of Traditional Chinese Medicine, Yunnan University of Traditional Chinese Medicine, Kunming 650500, China
Abstract:C-aryl glycosides(2a~2c) were stereoselectively synthesized by substitution reaction of 2, 3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide and aryl Grignard reagents, using THF as the solvent and CuI/TMEDA as the catalyst.The structures were confirmed by 1 H NMR and 13 C NMR.Under the optimized reaction conditions(THF as the solvent, 10%CuI and 10%TMEDA as the catalyst, and the reac-tion temperature was 0℃), the yields of 2a~2c were 58%~71%andα/βwere 1/6.5~1/7.1.
Keywords:CuI  catalysis  C-aryl glycoside  synthesis
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