Conformationally restricted oxazolidin‐2‐one fused bicyclic iminosugars as potential glycosidase inhibitors - Archive ouverte HAL Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2020

Conformationally restricted oxazolidin‐2‐one fused bicyclic iminosugars as potential glycosidase inhibitors

Abstract

The synthesis of fused bicyclic oxazolidin-2-one (OZO) iminosugars was achieved through a tandem Staudinger reduction/retro-Michael/intramolecular Michael addition from the corresponding OZO azidosugars. Those precursors, based on both aldopentofuranoses and ketofuranohexoses backbones, were obtained following alkylation and oxidation of the related oxazolidine-2-thione (OZT) azidosugars. Eight OZO based iminosugars were isolated in good yields and evaluated for their potency as glycosidases inhibitors, thus extending the family of known 1-Deoxynojirimycin (DNJ) bicyclic analogues.
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Dates and versions

hal-03478285 , version 1 (13-12-2021)

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Maria Domingues, Justyna Jaszczyk, Maria Isabel Ismael, José Albertino Figueiredo, Richard Daniellou, et al.. Conformationally restricted oxazolidin‐2‐one fused bicyclic iminosugars as potential glycosidase inhibitors. European Journal of Organic Chemistry, 2020, 2020 (38), pp.6109-6126. ⟨10.1002/ejoc.202001053⟩. ⟨hal-03478285⟩
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