1037070-99-7Relevant academic research and scientific papers
Synthesis of a nucleoside phosphoramidate prodrug inhibitor of HCV NS5B polymerase: Phenylboronate as a transient protecting group
Mayes, Benjamin A.,Arumugasamy, Jeevanandam,Baloglu, Erkan,Bauer, David,Becker, Alan,Chaudhuri, Narayan,Latham, G. Mark,Li, Jie,Mathieu, Steve,McGarry, F. Patrick,Rosinovsky, Elodie,Stewart, Alistair,Trochet, Christophe,Wang, Jingyang,Moussa, Adel
, p. 717 - 724 (2014)
A synthetic process for 2′-C-methylcytidine-5′-[2-[(3-hydroxy- 2,2-dimethyl-1-oxopropyl)thio]ethyl-N-benzylphosphoramidate], a nucleotide prodrug inhibitor of hepatitis C virus NS5B polymerase, is described. The route developed was demonstrated on 100 g scale and featured the key application of phenylboronic acid as an effective transient means to protect the 2′,3′-hydroxyls of 2′-C-methylcytidine. This synthetic methodology resulted in a reduction in the number of isolations from five to two and an increase in the overall yield by 50% relative to the original unscalable discovery route. The synthesis and characterization of 2′-C- methylcytidine-2′,3′-O-phenylboronate is also provided.
