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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 10: 3439 - 3445

DOI: https://doi.org/10.6023/cjoc202004052

A New Approach to the Synthesis of Acteoside

  • Hu Zhifei ,
  • Xu Peng ,
  • Yu Biao
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  • a School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210;
    b State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2020-04-30

  Revised date: 2020-05-13

  Online published: 2020-05-19

Supported by

Project supported by the National Key Research & Development Program of China (No. 2018YFC0310900), the National Natural Science Foundation of China (No. 21621002), the Key Research Program of Frontier Sciences of Chinese Academy of Sciences (No. ZDBS-LY-SLH030), the Strategic Priority Research Program of Chinese Academy of Sciences (No. XDB20020000), and the K. C. Wong Education Foundation.

Fold

Abstract

A new approach to the synthesis of acteoside, a prototypical phenylpropanoid glycoside with a variety of biological activities, has been developed. The synthesis employed a regioselective glycosylation as a key step, in which a gold(I)-catalyzed glycosylation of p-tolyl 6-O-acetyl-1-thio-β-D-glucopyranoside with peracetyl L-rhamnopyranosyl ortho-alkynylbenzoate led to the desired α-(1→3) linked disaccharide 7-1 in a satisfactory yield. The resultant disaccharide was converted into the corresponding ortho-alkynylbenzoate donor and subjected to glycosylation with aglycone, subsequent deprotection of the protecting groups furnished acteoside.

Key words： acteoside; phenylpropanoid glycoside; glycosylation; Au(I) catalysis

Cite this article

Hu Zhifei , Xu Peng , Yu Biao . A New Approach to the Synthesis of Acteoside[J]. Chinese Journal of Organic Chemistry, 2020 , 40(10) : 3439 -3445 . DOI: 10.6023/cjoc202004052

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