Citation: 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 shu

A New Approach to the Synthesis of Acteoside

Hu Zhifei ^a,b ,
Xu Peng ^b ,
Yu Biao ^a,b,,

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

Corresponding author: Yu Biao, byu@sioc.ac.cn
Received Date: 30 April 2020
Revised Date: 13 May 2020
Available Online: 19 May 2020
Fund Project: the National Key Research & Development Program of China 2018YFC0310900Project 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 Foundationthe Key Research Program of Frontier Sciences of Chinese Academy of Sciences ZDBS-LY-SLH030the National Natural Science Foundation of China 21621002the Strategic Priority Research Program of Chinese Academy of Sciences XDB20020000

Figures(2)

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.
- acteoside,
- phenylpropanoid glycoside,
- glycosylation,
- Au(I) catalysis
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