Synthesis of ABBV-168, a 2′-Bromouridine for the Treatment of Hepatitis C
- Eric A. Voight (2243263)
- Brian S. Brown (2375293)
- Stephen N. Greszler (2191588)
- Geoff T. Halvorsen (2408170)
- Gang Zhao (161405)
- Albert W. Kruger (1843555)
- John Hartung (359673)
- Kirill A. Lukin (2391709)
- Steven R. Martinez (2182504)
- Eric G. Moschetta (1369659)
- Michael T. Tudesco (5871617)
- Nathan D. Ide (2053966)
Publication date
November 2018
DOI Publisher
American Chemical Society (ACS)Abstract
ABBV-168 is a dihalogenated nucleotide under investigation for the treatment of hepatitis C virus. Three synthetic routes aimed at achieving the stereoselective installation of the C2′ gem-Br,F substitution and subsequent Vorbruggen glycosylation were explored to prepare the penultimate nucleoside intermediate. Development culminated in a route to ABBV-168 featuring a de novo chromatography-free furanose synthesis, protecting group-directed Vorbruggen glycosylation, and highly selective phosphoramidation to furnish the API
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