Boronic Acid-Assisted Site-Selective Benzylation of Unprotected Saccharides

Site-selective benzylation of specific hydroxyl groups (OH) in unprotected saccharides is crucial for the synthesis of complex saccharide-based pharmaceuticals. However, it remains a significant challenge due to the minimal reactivity differences among multiple chemically similar OH groups. Herein, we present a site-switchable, one-step synthetic benzylation strategy through strategically tuning the structure of boronic acids. This general and practical strategy establishes a framework for the rapid assembly of structurally diverse saccharide derivatives.

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Publication Details

Journal
Organic Letters
Published
2026-04-20
DOI
https://doi.org/10.1021/acs.orglett.6c00589
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
0.00

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article

Boronic Acid-Assisted Site-Selective Benzylation of Unprotected Saccharides

Wen‐Xin Lv, Shiqing Huang, Haiqi Wang, Yonggui Robin et al.
Organic Letters
Carbohydrate Chemistry and Synthesis
article

Boronic Acid-Assisted Site-Selective Benzylation of Unprotected Saccharides

Wen‐Xin Lv, Shiqing Huang, Haiqi Wang, Yonggui Robin, Chang Chin Ho, Liang Yang, Min Xu
article en

Abstract

Site-selective benzylation of specific hydroxyl groups (OH) in unprotected saccharides is crucial for the synthesis of complex saccharide-based pharmaceuticals. However, it remains a significant challenge due to the minimal reactivity differences among multiple chemically similar OH groups. Herein, we present a site-switchable, one-step synthetic benzylation strategy through strategically tuning the structure of boronic acids. This general and practical strategy establishes a framework for the rapid assembly of structurally diverse saccharide derivatives.

Organic LettersVol. 28(17)
Nanyang Technological University (SG), Guizhou University (CN), Affiliated Hospital of Guizhou Medical University (CN), Shanghai Pesticide Research Institute (CN), Renmin University of China (CN)
National Research Foundation Singapore, Ministry of Education - Singapore, Nanyang Technological University, National Natural Science Foundation of China, Guizhou University, Higher Education Discipline Innovation Project, Young Scientists Fund, National Key Research and Development Program of China
Openalex Percentile: Top 21%
Carbohydrate Chemistry and Synthesis
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Boronic Acid-Assisted Site-Selective Benzylation of Unprotected Saccharides — Wen‐Xin Lv, Shiqing Huang, et al. · Organic Letters (2026) | TGRS Research Map | TGRS