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. https://doi.org/10.3762/bxiv.2020.118.v1

Published 12 Oct 2020

  • Preprint

Abstract

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

Supporting Information

Format: CIF Size: 1.5 MB   Download
Format: CIF Size: 799.4 KB   Download
Format: PDF Size: 6.9 MB   Download

How to Cite

When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

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

Download Citation
Download RIS (Reference Manager) Download BIB (BIBTEX)

© 2020 Więcław and Furman; licensee Beilstein-Institut.
This is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.
The license is subject to the Beilstein Archives terms and conditions: (https://www.beilstein-archives.org/xiv/terms)

Other Beilstein-Institut Open Science Activities

Logo
Logo
Logo
Symposia