A New Approach to the Synthesis of Acteoside

doi:10.6023/cjoc202004052

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

Special Issue: 黄乃正院士七十华诞专辑

一条合成毛蕊花苷的新路线

胡志飞^a,b, 徐鹏^b, 俞飚^a,b

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 E-mail:byu@sioc.ac.cn
基金资助:
国家重点研发计划（No.2018YFC0310900）、国家自然科学基金（No.21621002）、中国科学院前沿科学重点研究（No.ZDBS-LY-SLH030）、中国科学院战略性先导科技专项（B类）（No.XDB20020000）和王宽诚教育基金会资助项目.

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

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.

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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

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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.

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一条合成毛蕊花苷的新路线

A New Approach to the Synthesis of Acteoside

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