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有机化学
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有机化学 ›› 2012, Vol. 32 ›› Issue (06): 1067-1071.DOI: 10.6023/cjoc1203021 上一篇    下一篇

研究论文

天然山奈酚5 位鼠李糖糖苷的高效合成

杨为准a,b, 李荣耀b, 韩伟a, 张卫东c, 孙建松b   

  1. a 华东理工大学药学院 上海 200237;
    b 中国科学院上海有机化学研究所生命有机国家重点实验室 上海 200032;
    c 第二军医大学药学院 上海 200433
  • 收稿日期:2012-03-02 修回日期:2012-03-20 发布日期:2012-04-10
  • 通讯作者: 韩伟, 张卫东, 孙建松 E-mail:jssun@sioc.ac.cn
  • 基金资助:
    国家自然科学基金(No. 20902097)资助项目.

Highly Efficient Synthesis of Kaempferol-5-O-rhamnopyranoside

Yang Weizhuna,b, Li Rongyaob, Han Weia, Zhang Weidongc, Sun Jiansongb   

  1. a School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China;
    b State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;
    c Department of Phytochemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433
  • Received:2012-03-02 Revised:2012-03-20 Published:2012-04-10
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 20902097)

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Kaempferol-5-O-α-L-rhamnopyranoside (1) 与 Kaempferol-3,5-di-O-α-L-rhamnopyranoside (2) 是一类具有代表性的黄酮醇5 位鼠李糖的天然化合物。由于5 位羟基具有较强的分子内氢键,传统的糖苷化条件不能高效合成。本文使用全新的糖苷化方法,以糖基邻炔基苯甲酸酯作给体,一价金作催化剂,高效的构建了山奈酚5 位的糖苷键,并完成了天然产物 1 和 2 的合成。

关键词: 山奈酚, 鼠李糖, 糖基邻炔基苯甲酸酯, 金催化, 糖苷化

Kaempferol-5-O-α-L-rhamnopyranoside (1) and Kaempferol-3,5-di-O-α-L-rhamnopyranoside (2) are representative flavonol 5-O-rhamnopyranoside. Because of the strong intramolecular H-bond, the 5-O-glucosidic linkage could not be efficiently constructed via conventional glycosylation method. In this paper, we use a novel glycosylation method which is gold (I)-catalyzed glycosylation method with glycosyl ortho-alkynylbenzoates as donor to efficiently achieve the formation of the challenging Kaempferol-5-O-glycosidic linkages, and finally leading to naturally occurring compounds 1 and 2.

Key words: kaempferol, rhamnose, glycosyl ortho-alkynylbenzoate, gold -catalyzed, glycosylation