有机化学 ›› 2006, Vol. 26 ›› Issue (06): 813-816. 上一篇    下一篇

研究论文

四种天然槲皮素-3-糖苷的合成

陈志卫,胡永洲*   

  1. (浙江大学药学院 杭州 310031)
  • 收稿日期:2005-06-24 修回日期:2005-12-08 发布日期:2006-05-31

Synthesis of Four Natural Quercetin-3-O-glycosides

CHEN Zhi-Wei,HU Yong-Zhou*   

  1. (Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310031)
  • Received:2005-06-24 Revised:2005-12-08 Published:2006-05-31

以芦丁为原料, 经苄基化、酸水解得到关键中间体3′,4′,7-O-三苄基槲皮素(3), 3与相应的1-溴代乙酰糖在四丁基溴化铵催化下在氯仿-0.25 mol•L-1 K2CO3溶液中缩合成相应的糖苷, 脱去保护基得天然槲皮素3-糖苷类化合物 1a~1d. 其结构经IR, 1H NMR, MS及元素分析确证.

关键词: 3′,4′,7-O-三苄基槲皮素, 相转移催化法, 合成, 槲皮素-3-糖苷

Benzylation of rutin followed by hydrolysis afforded 3′,4′,7-O-tribenzylquercetin (3). Compound 3 was condensed with acetylglycosyl bromides in a two-phase system of chloroform-0.25 mol•L-1 aqueous potassium carbonate using tetrabutyl ammonium bromide as catalyst to yield the protected glycosides 4a~4d. Removal of protecting group led to target products 1a1d and the structures of such products 1a~1d were confirmed by IR, 1H NMR, MS spectra and elemental analysis.

Key words: phase transfer catalysis, quercetin-3-O-glycoside, synthesis, 3′,4′,7-O-tribenzylquercetin