Novel intramolecular aminohydroxylation toward the syntheses of 2′-amino-2′-ethynyl nucleosides. (25th May 2021)

• Record Type: Journal Article
• Authors: Huang, Yuhua; Bennett, Frank; Buevich, Alexei; Girijavallabhan, Vinay; Kerekes, Angela D.; Huang, Hsueh-Cheng; Tawa, Paul; Bogen, Stephane L.; Davies, Ian W.
• Is Part Of: Tetrahedron letters. Volume 72(2021)
• Publication Date: 2021-05-25
• Subjects: Nucleoside -- HCV -- Triphosphate; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153066
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Tertiary amino nucleoside via tethered aminohydroxylation. Diastereospecificity. Nucleosides bearing ethynyl/amino at the C2′ position. Abstract: Syntheses of both 2′-amino-2′-ethynyl guanosine and uridine, using an intramolecular aminohydroxylation reaction as the key step, are described. The corresponding 5′- O -triphosphates of the aforementioned nucleosides were obtained and the inhibitory activity was subsequently evaluated against the hepatitis C virus NS5B polymerase.