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Chinese Journal of Organic Chemistry >

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

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

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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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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

Cite this article

Yang Weizhun , Li Rongyao , Han Wei , Zhang Weidong , Sun Jiansong . Highly Efficient Synthesis of Kaempferol-5-O-rhamnopyranoside[J]. Chinese Journal of Organic Chemistry, 2012 , 32(06) : 1067 -1071 . DOI: 10.6023/cjoc1203021

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