Photoinduced Palladium-Catalyzed Controllable Multicomponent Mono- or Di-C-glycosylation for the Construction of Alkyl <i>C</i> -Glycoconjugates

A general modular assembly strategy for the selective synthesis of alkyl C-glycoconjugates was reported via a photoinduced Pd-catalyzed multicomponent mono- or di-C-glycosylation from a variety of glycosyl radical precursors, feedstock 1,3-dienes, and readily available carbon-, oxygen-, nitrogen-, and sulfur-based nucleophiles. This protocol features mild conditions, good functional group tolerability, and excellent regio- and stereoselectivities. The strategy also provides a practical platform for the synthesis of diverse valuable C-glycosylated heterocycles, glyco-amino acids, glyco-peptides, glyco-lipids, and glyco-drug derivatives.

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Publication Details

Journal
Organic Letters
Published
2025-12-24
DOI
https://doi.org/10.1021/acs.orglett.5c04951
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
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article

Photoinduced Palladium-Catalyzed Controllable Multicomponent Mono- or Di-C-glycosylation for the Construction of Alkyl C -Glycoconjugates

Qiao Ren, Wenming Zhang, Qianfa Jia, Huayu Zhang et al.
Organic Letters
Carbohydrate Chemistry and Synthesis
article

Photoinduced Palladium-Catalyzed Controllable Multicomponent Mono- or Di-C-glycosylation for the Construction of Alkyl C -Glycoconjugates

Qiao Ren, Wenming Zhang, Qianfa Jia, Huayu Zhang, Jicheng Wu, Xianyu Chen, Xin Zhuang
article en

Abstract

A general modular assembly strategy for the selective synthesis of alkyl C-glycoconjugates was reported via a photoinduced Pd-catalyzed multicomponent mono- or di-C-glycosylation from a variety of glycosyl radical precursors, feedstock 1,3-dienes, and readily available carbon-, oxygen-, nitrogen-, and sulfur-based nucleophiles. This protocol features mild conditions, good functional group tolerability, and excellent regio- and stereoselectivities. The strategy also provides a practical platform for the synthesis of diverse valuable C-glycosylated heterocycles, glyco-amino acids, glyco-peptides, glyco-lipids, and glyco-drug derivatives.

Organic LettersVol. 28(1)
Southwest University (CN), Chongqing University (CN), Yangtze Normal University (CN), Pharmaceutical Biotechnology (Czechia) (CZ)
Openalex Percentile: Top 33%
Carbohydrate Chemistry and Synthesis
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