Synthetic Routes to Sofosbuvir

[1]  Martin D. Eastgate,et al.  Development of a Diastereoselective Phosphorylation of a Complex Nucleoside via Dynamic Kinetic Resolution. , 2015, The Journal of organic chemistry.

[2]  C. Mcguigan,et al.  Chemcomm Communication , 2022 .

[3]  R. Schinazi,et al.  Synthesis of Nucleoside Phosphate and Phosphonate Prodrugs , 2014, Chemical reviews.

[4]  H. Couthon-Gourvès,et al.  Atherton–Todd reaction: mechanism, scope and applications , 2014, Beilstein journal of organic chemistry.

[5]  J. Conrad,et al.  A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir , 2014, Journal of the American Chemical Society.

[6]  R. Koff Review article: the efficacy and safety of sofosbuvir, a novel, oral nucleotide NS5B polymerase inhibitor, in the treatment of chronic hepatitis C virus infection , 2014, Alimentary pharmacology & therapeutics.

[7]  N. Ford,et al.  Minimum Costs for Producing Hepatitis C Direct-Acting Antivirals for Use in Large-Scale Treatment Access Programs in Developing Countries , 2014, Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.

[8]  M. Manns,et al.  Novel therapies for hepatitis C — one pill fits all? , 2013, Nature Reviews Drug Discovery.

[9]  Junbiao Chang,et al.  A New Route for the Synthesis of 4-Amino-5-Fluoro-7-(2′-Deoxy-2′-Fluoro-2′-C-Methyl-β-d- Ribofuranosyl)-1H-Pyrrolo[2,3-D]Pyrimidine , 2013, Nucleosides, Nucleotides & Nucleic Acids.

[10]  M. Sofia Nucleotide prodrugs for the treatment of HCV infection. , 2013, Advances in pharmacology.

[11]  E. Clercq Milestones in the discovery of antiviral agents: nucleosides and nucleotides , 2012 .

[12]  Hanna Wójtowicz-Rajchel Synthesis and applications of fluorinated nucleoside analogues , 2012 .

[13]  C. Espiritu,et al.  A 2′-Deoxy-2′-Fluoro-2′-C-Methyl Uridine Cyclopentyl Carbocyclic Analog and Its Phosphoramidate Prodrug as Inhibitors of HCV NS5B Polymerase , 2012, Nucleosides, nucleotides & nucleic acids.

[14]  S. Samanta,et al.  Current perspective of HCV NS5B inhibitors: a review. , 2011, Current medicinal chemistry.

[15]  C. Espiritu,et al.  Synthesis of Stable Isotope Labeled Analogs of the Anti-Hepatitis C Virus Nucleotide Prodrugs PSI-7977 and PSI-352938 , 2011, Nucleosides, nucleotides & nucleic acids.

[16]  M. Sofia Nucleotide Prodrugs for HCV Therapy , 2011, Antiviral chemistry & chemotherapy.

[17]  M. Sofia,et al.  Synthesis of diastereomerically pure nucleotide phosphoramidates. , 2011, The Journal of organic chemistry.

[18]  J. Yoo,et al.  Synthesis of SATE Prodrug of 6'-Fluoro-6'-methyl-5'-noradenosine Nucleoside Phosphonic Acid as a New Class of Anti-HIV Agent , 2010 .

[19]  M. Otto,et al.  Discovery of a β-d-2'-deoxy-2'-α-fluoro-2'-β-C-methyluridine nucleotide prodrug (PSI-7977) for the treatment of hepatitis C virus. , 2010, Journal of medicinal chemistry.

[20]  Alan S. Perelson,et al.  Rapid Emergence of Protease Inhibitor Resistance in Hepatitis C Virus , 2010, Science Translational Medicine.

[21]  David R. Bill,et al.  Aminodifluorosulfinium Salts: Selective Fluorination Reagents with Enhanced Thermal Stability and Ease of Handling, , 2010, The Journal of organic chemistry.

[22]  J. Hong,et al.  Synthesis of 2′-Fluoro and 2′,4′-Dimethyl Pyrimidine C-Nucleoside Analogues as Potential Anti-HCV Agents , 2010, Nucleosides, nucleotides & nucleic acids.

[23]  Chien-Tien Chen,et al.  Substitution‐ and Elimination‐Free Phosphorylation of Functionalized Alcohols Catalyzed by Oxidomolybdenum Tetrachloride , 2010 .

[24]  J. Balzarini,et al.  Aryloxy Phosphoramidate Triesters: a Technology for Delivering Monophosphorylated Nucleosides and Sugars into Cells , 2009, ChemMedChem.

[25]  A. L’Heureux,et al.  Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents , 2009, Organic letters.

[26]  W. Stec,et al.  An efficient and diastereoselective synthesis of PSI-6130: a clinically efficacious inhibitor of HCV NS5B polymerase. , 2009, The Journal of organic chemistry.

[27]  T. P. Cleary,et al.  A practical synthesis of (2R)-3,5-di-O-benzoyl-2-fluoro-2-C-methyl-d-ribono-γ-lactone , 2009 .

[28]  M. Manns,et al.  The way forward in HCV treatment — finding the right path , 2007, Nature Reviews Drug Discovery.

[29]  M. Otto,et al.  The Mechanism of Action of β-d-2′-Deoxy-2′-Fluoro-2′-C-Methylcytidine Involves a Second Metabolic Pathway Leading to β-d-2′-Deoxy-2′-Fluoro-2′-C-Methyluridine 5′-Triphosphate, a Potent Inhibitor of the Hepatitis C Virus RNA-Dependent RNA Polymerase , 2007, Antimicrobial Agents and Chemotherapy.

[30]  Klaus Klumpp,et al.  Characterization of the Metabolic Activation of Hepatitis C Virus Nucleoside Inhibitor β-d-2′-Deoxy-2′-fluoro-2′-C-methylcytidine (PSI-6130) and Identification of a Novel Active 5′-Triphosphate Species* , 2007, Journal of Biological Chemistry.

[31]  G. Fleet,et al.  Anomeric stereospecific synthesis of 2'-C-methyl β-nucleosides; the Holy reaction of cyanamide with 2-C-methyl-D-arabinose , 2007 .

[32]  C. Mcguigan,et al.  Application of the phosphoramidate ProTide approach to 4'-azidouridine confers sub-micromolar potency versus hepatitis C virus on an inactive nucleoside. , 2007, Journal of medicinal chemistry.

[33]  M. Otto,et al.  Mechanism of Activation of β-d-2′-Deoxy-2′-Fluoro-2′-C-Methylcytidine and Inhibition of Hepatitis C Virus NS5B RNA Polymerase , 2007, Antimicrobial Agents and Chemotherapy.

[34]  R. Schinazi,et al.  Synthesis of 2‐Deoxy‐2‐Fluoro‐2‐C‐Methyl‐D‐Ribofuranoses , 2006 .

[35]  M. Otto,et al.  Synthesis and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methyl purine nucleosides as inhibitors of hepatitis C virus RNA replication. , 2006, Bioorganic & medicinal chemistry letters.

[36]  R. Storer,et al.  Amadori ketoses with calcium hydroxide and the Kiliani reaction on 1-deoxy ketoses : two approaches to the synthesis of saccharinic acids , 2006 .

[37]  W. Stec,et al.  Design, synthesis, and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methylcytidine, a potent inhibitor of hepatitis C virus replication. , 2005, Journal of medicinal chemistry.

[38]  M. Otto,et al.  SYNTHESIS AND IN VITRO ANTI-HCV ACTIVITY OF β-D- and L-2′-DEOXY-2′-FLUORORIBONUCLEOSIDES , 2005 .

[39]  Steven R. LaPlante,et al.  An NS3 protease inhibitor with antiviral effects in humans infected with hepatitis C virus , 2003, Nature.

[40]  K. Wareing,et al.  The Regiospecific One-Pot Phosphorylation of Either the 5′- or 2′-Hydroxyl in 3′-Deoxycytidines Without Protection: Critical Role of the Base , 2003, Nucleosides, Nucleotides & Nucleic Acids.

[41]  T. Lobl,et al.  An Improved Procedure for the Synthesis of Nucleoside Phosphoramidates , 2002 .

[42]  S. Shuto,et al.  Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-β-d-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbrüggen glycosylation reaction ☆ , 2002 .

[43]  C. Lee,et al.  C-4 EPIMERIZATION OF α-D-GLUCOPYRANOSIDE: A FACILE SYNTHESIS OF 4-O-ACETYL-α-D-GALACTOPYRANOSYL DERIVATIVES , 2001 .

[44]  R. Duguid,et al.  New Synthesis of a Protected Ketonucleoside by a Non-Cryogenic Oxidation with TFAA/DMSO1 , 2000 .

[45]  G. Elgemeie,et al.  Nucleic Acid Components and Their Analogues: New Synthesis of Bicyclic Thiopyrimidine Nucleosides , 2000, Nucleosides, nucleotides & nucleic acids.

[46]  M. Wolfe,et al.  A Short, Flexible Route toward 2‘-C-Branched Ribonucleosides , 1997 .

[47]  M. Wolfe,et al.  A concise synthesis of 2′-c-methylribonucleosides , 1995 .

[48]  R. Noyori,et al.  O-selective phosphorylation of nucleosides without N-protection , 1993 .

[49]  A. Hay,et al.  Aryl phosphate derivatives of AZT retain activity against HIV1 in cell lines which are resistant to the action of AZT. , 1992, Antiviral research.

[50]  A. Matsuda,et al.  Nucleosides and nucleotides. 97. Synthesis of new broad spectrum antineoplastic nucleosides, 2'-deoxy-2'-methylidenecytidine (DMDC) and its derivatives. , 1991, Journal of medicinal chemistry.

[51]  S. Bell,et al.  Oxoiron(IV) porphyrins derived from charged iron(III) tetraarylporphyrins and chemical oxidants in aqueous and methanolic solutions , 1991 .

[52]  R. Purcell,et al.  Hepatitis C virus shares amino acid sequence similarity with pestiviruses and flaviviruses as well as members of two plant virus supergroups. , 1990, Proceedings of the National Academy of Sciences of the United States of America.

[53]  V. Sayeed,et al.  A Simple and Convenient Method for the Selective N-Acylations of Cytosine Nucleosides , 1989 .

[54]  K. Sharpless,et al.  Vicinal diol cyclic sulfates. Like epoxides only more reactive , 1988 .

[55]  A. Matsuda,et al.  Alkyl addition reaction of pyrimidine 2'-ketonucleosides: synthesis of 2'-branched-chain sugar pyrimidine nucleosides (nucleosides and nucleotides. LXXXI. , 1988, Chemical & pharmaceutical bulletin.

[56]  S. Roberts,et al.  Use of diethylaminosulphur trifluoride (DAST) in the preparation of synthons of carbocyclic nucleosides , 1988 .

[57]  H. Hayakawa,et al.  Reaction of organometallic reagents with 2'- and 3'-ketouridine derivatives: Synthesis of uracil nucleosides branched at the 2'- and 3'-positions. , 1987 .

[58]  R. Klein,et al.  Nucleosides LXXXIX. Synthesis of 1-(2-chloro-2-deoxy-α- and -β-D-arabinofuranosyl)cytosines☆ , 1975 .

[59]  A. Holý A synthesis of 6-methyl-2′-deoxyuridine , 1973 .

[60]  J. G. Moffatt,et al.  Sulfoxide-carbodiimide reactions. VI. Synthesis of 2'-and 3'-ketouridines , 1967 .