Preparation of glycosyl carboxylic acids<i>via</i>stereoselective synthesis and oxidative cleavage of<i>C</i>-vinyl glycosides

Pan, Qiang; Zhou, Qi-Min; Rui, Peixin; Hu, Xiang‐Guo

doi:10.1039/d2ob00896c

Org. Biomol. Chem.

2022

DOI: 10.1039/d2ob00896c

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Preparation of glycosyl carboxylic acidsviastereoselective synthesis and oxidative cleavage ofC-vinyl glycosides

Qiang Pan

Qi-Min Zhou

Peixin Rui

et al.

Abstract: We have developed an improved cyanide-free strategy for the synthesis of glycosyl carboxylic acids, employing stereoselective C-vinyl glycosylation and oxidative cleavage of C-vinyl glycosides as key steps. Compared to our...

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Cited by 4 publications

References 68 publications

(36 reference statements)

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Generation and Use of Glycosyl Radicals under Acidic Conditions: Glycosyl Sulfinates as Precursors

Zhang

et al. 2023

Angewandte Chemie

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We herein report a method that enables the generation of glycosyl radicals under highly acidic conditions. Key to the success is the design and use of glycosyl sulfinates as radical precursors, which are bench-stable solids and can be readily prepared from commercial starting materials. This development allows the installation of glycosyl units onto pyridine rings directly by the Minisci reaction. We further demonstrate the utility of this method in the late-stage modification of complex drug molecules, including the anticancer agent camptothecin. Experimental studies provide insight into the reaction mechanism.

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Generation and Use of Glycosyl Radicals under Acidic Conditions: Glycosyl Sulfinates as Precursors

Zhang

et al. 2023

Angewandte Chemie

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Generation and Use of Glycosyl Radicals under Acidic Conditions: Glycosyl Sulfinates as Precursors

Zhang

et al. 2023

Angew Chem Int Ed

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Glycosyl Radical-Based Synthesis of C-Alkyl Glycosides Bearing a Cyclopropane via a Deoxygenative Giese Addition–Reduction–Cyclization Cascade

Pang,

Feng,

Zhang

et al. 2024

Org. Lett.

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Preparation of glycosyl carboxylic acidsviastereoselective synthesis and oxidative cleavage ofC-vinyl glycosides

Abstract: We have developed an improved cyanide-free strategy for the synthesis of glycosyl carboxylic acids, employing stereoselective C-vinyl glycosylation and oxidative cleavage of C-vinyl glycosides as key steps. Compared to our...

Cited by 4 publications

References 68 publications

Generation and Use of Glycosyl Radicals under Acidic Conditions: Glycosyl Sulfinates as Precursors

Generation and Use of Glycosyl Radicals under Acidic Conditions: Glycosyl Sulfinates as Precursors

Generation and Use of Glycosyl Radicals under Acidic Conditions: Glycosyl Sulfinates as Precursors

Glycosyl Radical-Based Synthesis of C-Alkyl Glycosides Bearing a Cyclopropane via a Deoxygenative Giese Addition–Reduction–Cyclization Cascade

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