Site-Selective Debenzylation of C -Allyl Iminosugars Enables Their Stereocontroled Structure Diversification at the C-2 Position - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2019

Site-Selective Debenzylation of C -Allyl Iminosugars Enables Their Stereocontroled Structure Diversification at the C-2 Position

Résumé

A C-2 regioselective debenzylative cycloetherification/reductive elimination sequence applied to perbenzylated C-allyl iminosugars is described. This NIS/TMSOTf-triggered deprotection was successfully applied to five-, six-, and seven-membered C-allyl iminosugars including 1,2 cis and 1,2 trans stereoisomers. It allows rapid introduction of structural diversity at the key C-2 position in a stereoselective manner exploiting the anchimeric assistance of the intracyclic N-benzyl group, giving access to the 2-acetamido and 2-fluoro d-gluco configured C-allyl iminosugars and to the epimeric d-manno derivative.

Domaines

Chimie
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Dates et versions

hal-04418300 , version 1 (25-01-2024)

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Citer

Quentin Foucart, Jérôme Marrot, Jérôme Désiré, Yves Blériot. Site-Selective Debenzylation of C -Allyl Iminosugars Enables Their Stereocontroled Structure Diversification at the C-2 Position. Organic Letters, 2019, 21 (12), pp.4821-4825. ⟨10.1021/acs.orglett.9b01712⟩. ⟨hal-04418300⟩
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