An Efficient Synthetic Methodology for the Preparation of Glycosyl β‐diketones

Abstract In this study, we present a synthetic methodology for preparing glycosyl β‐diketones from the corresponding allyl ethers. The process involves three steps: nitrile oxide cycloadditions, reduction of the glycosyl isoxazolines, and oxidation of β‐hydroxyketones. This route is suitable for acid‐ and base‐sensitive protecting groups, and the reactions were conducted with retention of the anomeric configuration. The resulting glycosyl β‐diketones were then utilized in the synthesis of the corresponding pyrazoles.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2024-12-23
DOI
https://doi.org/10.1002/ejoc.202401366
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
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article

An Efficient Synthetic Methodology for the Preparation of Glycosyl β‐diketones

Ivan A. Barri, Macarena S. Le Pors, Pedro A. Colinas
European Journal of Organic Chemistry
Carbohydrate Chemistry and Synthesis
article

An Efficient Synthetic Methodology for the Preparation of Glycosyl β‐diketones

Ivan A. Barri, Macarena S. Le Pors, Pedro A. Colinas
article en

Abstract

Abstract In this study, we present a synthetic methodology for preparing glycosyl β‐diketones from the corresponding allyl ethers. The process involves three steps: nitrile oxide cycloadditions, reduction of the glycosyl isoxazolines, and oxidation of β‐hydroxyketones. This route is suitable for acid‐ and base‐sensitive protecting groups, and the reactions were conducted with retention of the anomeric configuration. The resulting glycosyl β‐diketones were then utilized in the synthesis of the corresponding pyrazoles.

European Journal of Organic ChemistryVol. 28(12)
Centro de Estudos de Cultura Contemporânea (BR), Universidad Nacional de La Plata (AR)
Clean water and sanitation
Openalex Percentile: Top 82%
Carbohydrate Chemistry and Synthesis
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