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2012 , Vol. 32 >Issue 06: 1067 - 1071

DOI: https://doi.org/10.6023/cjoc1203021

研究论文

天然山奈酚5 位鼠李糖糖苷的高效合成

  • 杨为准 ,
  • 李荣耀 ,
  • 韩伟 ,
  • 张卫东 ,
  • 孙建松
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  • 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

  网络出版日期: 2012-04-10

基金资助

国家自然科学基金(No. 20902097)资助项目.

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Highly Efficient Synthesis of Kaempferol-5-O-rhamnopyranoside

  • Yang Weizhun ,
  • Li Rongyao ,
  • Han Wei ,
  • Zhang Weidong ,
  • Sun Jiansong
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  • 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 date: 2012-03-02

  Revised date: 2012-03-20

  Online published: 2012-04-10

Supported by

Project supported by the National Natural Science Foundation of China (No. 20902097)

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摘要

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

本文引用格式

杨为准 , 李荣耀 , 韩伟 , 张卫东 , 孙建松 . 天然山奈酚5 位鼠李糖糖苷的高效合成[J]. 有机化学, 2012 , 32(06) : 1067 -1071 . DOI: 10.6023/cjoc1203021

Abstract

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

参考文献

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