Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams

  1. Michał Mateusz WięcławORCID Logo and
  2. Bartłomiej FurmanORCID Logo

Submitting author affiliation: Polish Academy of Sciences, Warsaw, Poland

Beilstein Arch. 2020, 2020118.

Published 12 Oct 2020

  • Preprint


Herein we present the direct asymmetric synthesis of tetrazole-functionalized 1-deoxynojirimycin derivatives from simple sugars via a Schwartz’s reagent-mediated reductive amide functionalization followed by a variant of the Ugi-azide multi-component reaction. The anomeric configurations of two products were unambiguously confirmed by X-ray analysis. This work also describes examples of interesting further transformations of the title products. Finally, some surprising observations regarding the mechanism of their formation were made.

Keywords: amide functionalization; iminosugars; Schwartz’s reagent; tetrazole

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Więcław, M. M.; Furman, B. Beilstein Arch. 2020, 2020118. doi:10.3762/bxiv.2020.118.v1

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© 2020 Więcław and Furman; licensee Beilstein-Institut.
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