Stereoselective synthesis of iminosugar-C-glycosides through addition of organometallic reagents to N-tert-butanesulfinyl glycosylamines: A comprehensive study - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue (Article De Synthèse) European Journal of Organic Chemistry Année : 2023

Stereoselective synthesis of iminosugar-C-glycosides through addition of organometallic reagents to N-tert-butanesulfinyl glycosylamines: A comprehensive study

Synthèse stéréosélective d'iminosucre-C-glycosides par addition de réactifs organométalliques sur des N-tert-butanesulfinyl glycosylamines

Résumé

A comprehensive study of the preparation and reactivity of N-tert-butanesulfinyl glycosylamines with simple Grignard and organo lithium reagents in batch vs. continuous flow chemistry is reported. As they readily react as latent imine equivalents with a variety of carbon nucleophiles, these carbohydrate derivatives constitute very useful precursors for the diastereoselective synthesis of bioactive compounds such as iminosugar-C-glycosides. A hybrid protocol, involving the addition of benzylmagnesium chloride to a (SR)arabinofuranosylamine substrate in flow, at room temperature, combined with a cyclization protocol in batch is also described for the first time. Of note, this semi-continuous flow process shortens the synthesis of imino-C-glycoside scaffolds to a single workday
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Dates et versions

hal-04272030 , version 1 (06-11-2023)

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Daniel Kamzol, Maxime Neuville, Chloé Cocaud, Baptiste Taffoureau, Krzysztof Lewiński, et al.. Stereoselective synthesis of iminosugar-C-glycosides through addition of organometallic reagents to N-tert-butanesulfinyl glycosylamines: A comprehensive study. European Journal of Organic Chemistry, 2023, 2023, pp.e202300762. ⟨10.1002/ejoc.202300762⟩. ⟨hal-04272030⟩
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