Minimally Protected and Stereoselective <i>O</i>-Glycosylation of Carboxylic Acid Allows Rapid Access to α-1-<i>O</i>- and 2-<i>O</i>-Acyl Glycosides

We herein reported a catalytic, minimally protected, and highly α-stereoselective glycosylation protocol using carboxylic acid as an acceptor and glycosyl 8-alkynyl-1-naphthoate as a donor, enabling efficient access to unprotected α-1-<i>O</i>- and 2-<i>O</i>-acyl glycosides. This method demonstrates excellent functional compatibility and scope generality, allowing for the glycosylation of a wide range of complex carboxylic acids. Notably, we successfully synthesized two natural products, α-penta-<i>O</i>-galloyl-d-glucopyranose and nyctanthesin A, using this protocol. Mechanistic studies highlighted the crucial role of the 1-<i>O</i> ester functionality in ensuring chemoselectivity and the important contribution of the 2-<i>O</i> functionality in facilitating the reaction.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2025-03-31
DOI
https://doi.org/10.1021/jacs.5c01845
Citations
9
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
8.42

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article

Minimally Protected and Stereoselective O-Glycosylation of Carboxylic Acid Allows Rapid Access to α-1-O- and 2-O-Acyl Glycosides

Rongxia Li, Yugen Zhu, Baolong Hao, Yingjie Wang et al.
9 citations
Journal of the American Chemical Society
Carbohydrate Chemistry and Synthesis
8.42
article

Minimally Protected and Stereoselective O-Glycosylation of Carboxylic Acid Allows Rapid Access to α-1-O- and 2-O-Acyl Glycosides

Rongxia Li, Yugen Zhu, Baolong Hao, Yingjie Wang, Panpan Wang, Xiaojuan Zhang, Peng Xu, Xiaolong Li, Qian Zhang, Xinhao Zhu
article en
9 citations

Abstract

We herein reported a catalytic, minimally protected, and highly α-stereoselective glycosylation protocol using carboxylic acid as an acceptor and glycosyl 8-alkynyl-1-naphthoate as a donor, enabling efficient access to unprotected α-1-<i>O</i>- and 2-<i>O</i>-acyl glycosides. This method demonstrates excellent functional compatibility and scope generality, allowing for the glycosylation of a wide range of complex carboxylic acids. Notably, we successfully synthesized two natural products, α-penta-<i>O</i>-galloyl-d-glucopyranose and nyctanthesin A, using this protocol. Mechanistic studies highlighted the crucial role of the 1-<i>O</i> ester functionality in ensuring chemoselectivity and the important contribution of the 2-<i>O</i> functionality in facilitating the reaction.

Journal of the American Chemical SocietyVol. 147(16)
Guangzhou University of Chinese Medicine (CN), Nanjing University of Chinese Medicine (CN), Guangxi University (CN), Zunyi Medical University (CN), Chinese Academy of Sciences (CN), Shanghai Institute of Materia Medica (CN), University of Chinese Academy of Sciences (CN), Zhuhai Institute of Advanced Technology (CN)
National Natural Science Foundation of China, Guangdong Science and Technology Department, Zhongshan Science and Technology Bureau
Openalex Percentile: Top 2%
Carbohydrate Chemistry and Synthesis
8.42
DOISourceOpenAlex
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