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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (2): 321-324. 上一篇    下一篇

研究简报

溴代芳香碳糖苷的高效合成方法

张云志，陈冠宇，陈国荣*   

  1. (华东理工大学精细化工研究所 结构可控先进功能材料及其制备教育部重点实验室 上海 200237)
  • 收稿日期:2007-04-12 修回日期:2007-07-14 发布日期:2008-02-01
  • 通讯作者: 陈国荣

An Efficient Synthesis of Brominated C-Aryl Glycopyranoside

ZHANG Yun-Zhi,CHEN Guan-Yu,CHEN Guo-Rong*   

  1. (Laboratory for Advanced Materials, Institute of Fine Chemical, East China University of Science and Technology,
    Shanghai 200237)
  • Received:2007-04-12 Revised:2007-07-14 Published:2008-02-01
  • Contact: CHEN Guo-Rong

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被引次数

2

首先在三氟乙酸银和无水四氯化锡体系中合成芳香碳糖苷2-(2,3,4,6-四-O-乙酰基-β-D-吡喃糖)-1,4-二甲氧基苯(4a和4b), 再以弱路易斯酸硝酸铵为催化剂, 使用N-溴代丁二酰亚胺(NBS)在温和条件下溴化4a和4b, 高产率地得到2-(2,3,4,6-四-O-乙酰基-β-D-吡喃糖)-5-溴-1,4-二甲氧基苯(1a和1b); 讨论了NBS和硝酸铵的用量对溴化反应的影响, 并对产物的NMR进行了解析.

关键词: 芳香碳糖苷, N-溴代丁二酰亚胺, 硝酸铵, 溴化

Using SnCl4 and CF3CO2Ag as catalysts, 2-(2,3,4,6-tetra-O-acetyl-β-D-glycopyranosyl)-1,4- dimethoxy-benzenes (4a and 4b) were prepared firstly, then using NH4NO3 as a catalyst under milder condition the bromination of 4a or 4b by N-bromosuccinimide (NBS) gave 2-(2,3,4,6-tetra-O-acetyl-β-D-gly-copyranosyl)-5-bromo-1,4-dimethoxy-benzene (1a or 1b) in high yields. The effect of the quantity of NBS and NH4NO3 on the bromination was discussed.

Key words: N-bromosuccinimide, C-aryl glycoside, ammonium nitrate, bromination