有机化学 ›› 2009, Vol. 29 ›› Issue (01): 78-81. 上一篇    下一篇

研究论文

高效合成氯代苯醌基碳糖苷

李军廷; 郑蓉蓉; 张云志; 吕 遐; 唐燕辉*; 王朝霞*   

  1. (华东理工大学结构可控先进功能材料及其制备教育部重点实验室 精细化工研究所 上海 200237)
  • 收稿日期:2008-05-19 修回日期:2008-07-10 发布日期:2009-01-20
  • 通讯作者: 唐燕辉*; 王朝霞*

Efficient Synthesis of m-Chlorobenzoquinonyl C-Glycopyranosides

Li, Junting; Zheng, Rongrong ; Zhang, Yunzhi ;Lü, Xia; Tang, Yanhui*; Wang, Zhaoxia*
  

  1. (Laboratory for Advanced Materials, Institute of Fine Chemicals, East China University of
    Science and Technology, Shanghai 200237)
  • Received:2008-05-19 Revised:2008-07-10 Published:2009-01-20
  • Contact: Tang, Yanhui*; Wang, Zhaoxia*

报道一种简便、高效的氯代苯醌碳糖苷3a (3b)的合成新方法: 以苯醌基碳苷1a (1b)为原料, 经CH3COCl/THF/H2O体系进行加成反应, 高区域选择性获得糖基间位氯代的氢醌基碳苷2a (2b), 继而通过硝酸铈铵(CAN)氧化得到目标结构3a (3b), 并对所合成的化合物进行了结构表征.

关键词: 氯化, 苯醌, 氢醌, 芳香碳糖苷

A convenient and efficient synthesis of m-chlorobenzoquinonyl C-glycopyranosides 3a and 3b is reported. m-Chlorinated hydroquinonyl C-glycopyranosides 2a and 2b were synthesized by the addition of benzoquinone compounds 1a and 1b with CH3COCl/THF/H2O in high regioselectivities. Then the target compounds 3a and 3b were obtained after oxidation with ceric ammonium nitrate (CAN). The structures of the target compounds and intermediates were confirmed.

Key words: benzoquinone, chlorination, hydroquinone, aryl C-glycoside