Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3439-3445.DOI: 10.6023/cjoc202004052 Previous Articles     Next Articles


胡志飞a,b, 徐鹏b, 俞飚a,b   

  1. a 上海科技大学物质科学与技术学院 上海 201210;
    b 中国科学院上海有机化学研究所 生命有机化学国家重点实验室 上海 200032
  • 收稿日期:2020-04-30 修回日期:2020-05-13 发布日期:2020-05-20
  • 通讯作者: 俞飚
  • 基金资助:

A New Approach to the Synthesis of Acteoside

Hu Zhifeia,b, Xu Pengb, Yu Biaoa,b   

  1. 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:2020-04-30 Revised:2020-05-13 Published:2020-05-20
  • 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.

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