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Catalytic Asymmetric Synthesis of the anti-COVID-19 Drug Remdesivir.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2020 Nov 16; Vol. 59 (47), pp. 20814-20819. Date of Electronic Publication: 2020 Oct 08. - Publication Year :
- 2020
-
Abstract
- The catalytic asymmetric synthesis of the anti-COVID-19 drug Remdesivir has been realized by the coupling of the P-racemic phosphoryl chloride with protected nucleoside GS441524. The chiral bicyclic imidazole catalyst used is crucial for the dynamic kinetic asymmetric transformation (DyKAT) to proceed smoothly with high reactivity and excellent stereoselectivity (96 % conv., 22:1 S <subscript>P</subscript> :R <subscript>P</subscript> ). Mechanistic studies showed that this DyKAT is a first-order visual kinetic reaction dependent on the catalyst concentration. The unique chiral bicyclic imidazole skeleton and carbamate substituent of the catalyst are both required for the racemization process, involving the phosphoryl chloride, and subsequent stereodiscriminating step. A 10 gram scale reaction was also conducted with comparably excellent results, showing its potential for industrial application.<br /> (© 2020 Wiley-VCH GmbH.)
- Subjects :
- Adenosine Monophosphate chemical synthesis
Adenosine Monophosphate chemistry
Alanine chemical synthesis
Alanine chemistry
Antiviral Agents chemistry
Antiviral Agents therapeutic use
COVID-19 virology
Catalysis
Humans
Imidazoles chemistry
Kinetics
Molecular Conformation
SARS-CoV-2 isolation & purification
Stereoisomerism
COVID-19 Drug Treatment
Adenosine Monophosphate analogs & derivatives
Alanine analogs & derivatives
Antiviral Agents chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 59
- Issue :
- 47
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 32870563
- Full Text :
- https://doi.org/10.1002/anie.202011527