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  Direct and Catalytic C-Glycosylation of Arenes: Expeditious Synthesis of the Remdesivir Nucleoside

Obradors, C., Mitschke, B., Aukland, M. H., Leutzsch, M., Grossmann, O., Brunen, S., et al. (2022). Direct and Catalytic C-Glycosylation of Arenes: Expeditious Synthesis of the Remdesivir Nucleoside. Angewandte Chemie International Edition, 61(11): e202114619. doi:10.1002/anie.202114619.

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Obradors-Mitschke-Aukland-Leutzsch-Grossmann-Brunen-Schwengers-List.pdf (Publisher version), 2MB
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 Creators:
Obradors, Carla1, Author              
Mitschke, Benjamin1, Author              
Aukland, Miles H.1, Author              
Leutzsch, Markus2, Author              
Grossmann, Oleg1, Author              
Brunen, Sebastian1, Author
Schwengers, Sebastian A.1, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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Free keywords: Glycosylation; C-glycosides; Silylium catalysis; Remdesivir
 Abstract: Since early 2020, scientists have strived to find an effective solution to fight SARS-CoV-2, especially by developing reliable vaccines that inhibit the spread of the disease and repurposing drugs for combatting its effects on the human body. The antiviral prodrug Remdesivir is still the most widely used therapeutic during the early stage of the infection. However, the current synthetic routes rely on the use of protecting groups, air-sensitive reagents, and cryogenic conditions, impeding the cost-efficient supply to patients. We therefore focused on the development of a straightforward, direct addition of (hetero)arenes to unprotected sugars. Here we report a silylium-catalyzed and completely stereoselective C -glycosylation that initially yields the open-chain polyols, which can be selectively cyclized to provide either the kinetic α-furanose or the thermodynamically favored β-anomer. The method significantly expedites the synthesis of Remdesivir precursor GS-441524 after subsequent Mn-catalyzed C–H oxidation and deoxycyanation.

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Language(s): eng - English
 Dates: 2021-10-282021-12-012022-03-07
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202114619
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 61 (11) Sequence Number: e202114619 Start / End Page: - Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851