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DOI: 10.1055/a-2283-0623
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Carbohydrate Chemistry in China

Advances on the Synthesis of C-Aryl-glycosides Since 2019

Jiagen Li
a   Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. of China
,
Xuefeng Jiang  ∗
a   Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. of China
b   School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P. R. of China
c   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
› Author AffiliationsThe authors are grateful for financial support provided by the National Natural Science Foundation of China (NSFC) (22125103), the Science and Technology Commission of Shanghai Municipality (STCSM) (22JC1401000), and the China Postdoctoral Science Foundation (2023M731094 and BX20230127).
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Abstract

Aryl-glycosides represent a significant subclass of crucial glycosidic compounds, increasingly capturing the attention of pharmaceutical developers as bioelectronic motifs embedded within glycosides. Their outstanding resistance to enzymatic hydrolysis bestows a distinctive advantage in the field of drug development, particularly in therapeutic domains such as diabetes treatment, where pharmaceuticals based on the C-aryl-glycoside architecture manifest compelling therapeutic efficacy. As a result, researchers in the realm of synthetic chemistry have diligently explored and devised a plethora of streamlined and efficacious synthetic methodologies. This comprehensive account systematically delineates methodologies employed in recent years for the efficient synthesis of C-aryl-glycosides, offering insights into three primary directions: transition-metal catalysis, radical strategies, and metal-free catalysis processes.

1 Introduction

2 Glycosylation via Transition-Metal Catalytic Approaches

3 Glycosylation via Glycosyl Radical Approaches

4 Glycosylation via Metal-Free Catalytic Approaches

5 Conclusion and Outlook

Key words

C-aryl-glycosides - glycosylation - transition-metal catalysis - glycosyl radical - metal-free catalysis


Publication History

Received: 21 January 2024

Accepted after revision: 07 March 2024

Accepted Manuscript online:
07 March 2024

Article published online:
20 March 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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