Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams

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

Beilstein Arch. 2020, 2020118.

Published 12 Oct 2020

cc-by Logo


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

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.