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Synfacts 2020; 16(07): 0765
DOI: 10.1055/s-0040-1707019
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Remdesivir (GS-5734) — A Candidate for the Treatment of Ebola and COVID-19 Infections

Contributor(s):
Philip Kocienski
Cihlar T. * Bavari S. * et al. Gilead Sciences, Foster City and United States Army Medical Research Institute of Infectious Diseases, Frederick, USA
Therapeutic Efficacy of the Small Molecule GS-5734 Against Ebola Virus in Rhesus Monkeys.

Nature 2016;
531: 381-385
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Further Information

Publication History

Publication Date:
17 June 2020 (online)

 
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Key words

remdesivir - GS-5734 - COVID-19 - C-nucleoside - phosphoramidate prodrug - cyanation - pyrrolotriazinamine

Significance

Remdesivir (GS-5734) is a C-nucleoside phosphoramidate prodrug of an adenosine analogue discovered by workers at Gilead, that is of intense interest for the treatment of Ebola virus disease, COVID-19, and other lethal viruses. It is an RNA-dependent RNA polymerase inhibitor.


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Comment

The key step in the short synthesis ­depicted entails the construction of 1′-cyano C-glycoside F by reaction of O,O-acetal E with trimethylsilylcyanide (dr > 95:5). The presence of the 1′-cyano modification was critical in providing selectivity toward viral polymerases. See also: D. Siegel et al. J. Med. Chem. 2017, 60, 1648.


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