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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (9): 1243-1247. 上一篇    下一篇

研究论文

Lewis酸催化下2-(2,3,5-三-O-苯甲酰基-D-呋喃核糖)-1,4-氢醌的合成

何立，徐信，任志华，朱晨江，唐燕辉，陈国荣*   

  1. (华东理工大学精细化工研究所 上海 200237)
  • 收稿日期:2005-12-08 修回日期:1900-01-01 发布日期:2006-09-11
  • 通讯作者: 陈国荣

Synthesis of 2-(2,3,5-Tri-O-benzoyl-D-ribofuranosyl)-1,4-hydro-quinone with the Catalysis of Lewis Acids

HE Li,XU Xin,REN Zhi-Hua,ZHU Chen-Jiang
TANG Yan-Hui,CHEN Guo-Rong*   

  1. (Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237)
  • Received:2005-12-08 Revised:1900-01-01 Published:2006-09-11
  • Contact: CHEN Guo-Rong

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在不同Lewis酸催化下, 使用1,4-二苯酚和1-O-乙酰基-2,3,5-三-O-β-D-呋喃核糖进行反应, 以较高产率合成了α和β型芳香呋喃糖苷, 并利用1H-1H NOESY谱对2-(2,3,5-三-O-苯甲酰基-D-呋喃核糖)-1,4-氢醌(5)的立体构型进行了表征. 应用无水AlCl3, ZnCl2和BF3•Et2O等Lewis酸催化剂仅得到β型氧糖苷3, 应用TiCl4得到β型氧糖苷3以及α和β型碳糖苷的混合物5, 而应用SnCl4则得到α和β型碳糖苷5.

关键词: Lewis酸, 立体构型, 合成, 呋喃糖苷

Reactions of 1,4-dihydroquinone with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose in the presence of different Lewis acids afforded α- and β-aromatic ribofuranosides with good yield, and the stereocon-figuration of 2-(2,3,5-tri-O-benzoyl-D-ribofuranosyl)-1,4-hydroquinone (5) was confirmed by 1H-1H NOESY spectrum. Reactions catalyzed by anhy-drous AlCl3, ZnCl2 or BF3•Et2O gave β-O-ribofuranoside 3, whereas TiCl4 afforded a mixture of β-O-ribofuranoside (3) and α- and β-C-ribofuranosides (5), while SnCl4 produced the α- and β-C-ribofuranosides (5).

Key words: stereoconfiguration, ribofuranoside, Lewis acid, synthesis