Clevudine

Base Information

• Chemical Name: Clevudine
• CAS No.: 69256-17-3
• Molecular Formula: C10H13 F N2 O5
• Molecular Weight: 260.222
• Hs Code.: 2934999090
• UNII: 37F7D05ANB
• Nikkaji Number: J61.760A
• Wikipedia: Clevudine
• Wikidata: Q76005817
• NCI Thesaurus Code: C95210
• ChEMBL ID: CHEMBL475717
• Mol file: 69256-17-3.mol

Synonyms:1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione,;1-(2-deoxy-2-fluoro-beta-L-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione;1-(2-fluoro-2-deoxy-beta-arabinofuranosyl)thymine;1-(2-fluoro-2-deoxy-beta-D-arabinofuranosyl)thymine;1-(2-fluoro-5-methyl-beta,L-arabinofuranosyl)uracil;1-(2-fluoro-beta-L-arabinofuranosyl)thymine;2'-deoxy-2'-fluoroarabinofuranosylthymine;2'-fluoro-5-methyl-1-beta-D-arabinofuranosyluracil;2'-fluoro-5-methylarabinosyluracil;2'-fluoro-5-methylarabinosyluracil, 2-(14)C-labeled;5-methyl-2'-fluoroarauracil;Clevudine;D-FMAU;FMAU;L-FMAU

Chemical Property of Clevudine

Chemical Property:

• PKA: 9.55±0.10(Predicted)
• PSA: 104.55000
• Density: 1.55 g/cm3
• LogP: -1.56630
• Storage Temp.: 2-8°C
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 260.08084968
• Heavy Atom Count: 18
• Complexity: 413

Purity/Quality:

98%,99%, ^*data from raw suppliers

2''-Fluoro-5-methyl-1-β-D-arabinofuranosyluracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)F
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)F
• Recent ClinicalTrials: ANRS HB 05 Multicenter Study Evaluating Efficacy and Safety of Clevudine Monotherapy Versus Tenofovir Monotherapy Versus Combination Therapy of Clevudine and Tenofovir for 96 Weeks in HBeAg Negative Patients With Chronic Hepatitis B, na?ve to Anti-VHB Therapy
• Recent EU Clinical Trials: A randomized, double blind, multicenter study evaluating efficacy and safety of Clevudine monotherapy versus Tenofovir monotherapy versus combination therapy of Clevudine and Tenofovir for 96 weeks in HBeAg negative patients with chronic hepatitis B, na?ve to anti-VHB therapy
• Description: 2'-Fluoro-5-methyl-1-beta-D-arabinofuranosyluracil is the impurity of antiviral drug Clevudine (C574150), which is used for the treatment of Hepatitis B.
• Uses: 2''-Fluoro-5-methyl-1-β-D-arabinofuranosyluracil is the impurity of antiviral drug Clevudine (C574150), which is used for the treatment of Hepatitis B.

Technology Process of Clevudine

There total 18 articles about Clevudine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)thymine (97614-47-6) → 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine (69256-17-3,163252-36-6,2923-73-1)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1021/acs.orglett.6b03626

Reference yield:

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine (69256-17-3,163252-36-6,2923-73-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 83 percent / [bis(2-methoxyethyl)amino]sulfur trifluoride / CH₂Cl₂ / 50 °C

2.1: 90 percent / HBr / CH₂Cl₂ / 24 h / 20 °C

3.1: CCl₄ / 72 h / 77 °C

3.2: NH₄OH / methanol / 24 h / 20 °C

With hydrogen bromide; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In tetrachloromethane; dichloromethane;

DOI:10.1081/NCN-120022961

Reference yield:

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine (69256-17-3,163252-36-6,2923-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / HBr / CH₂Cl₂ / 24 h / 20 °C

2.1: CCl₄ / 72 h / 77 °C

2.2: NH₄OH / methanol / 24 h / 20 °C

With hydrogen bromide; In tetrachloromethane; dichloromethane;

DOI:10.1081/NCN-120022961

upstream raw materials:

1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)thymine

1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methylcytosine

1-(3',5'-di-O-benzoyl-2'-fluoro-2'-deoxy-α/β-D-arabinofuranosyl)thymine

2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide

Downstream raw materials:

1-(2-deoxy-2-fluoro-3-O-(methylsulfonyl)-5-O-trityl-β-D-arabinofuranosyl)thymine

1-(2-deoxy-2-fluoro-3-O-mesyl-5-O-triphenylmethyl-β-D-arabinofuranosyl)thymine

1-<5-O-(monomethoxytrityl)-2-fluoro-2-deoxy-β-D-arabinofuransosyl>thymine

2,3'-anhydro-1-(2-deoxy-2-fluoro-5-O-trityl-β-D-lyxofuranosyl)thymine

Refernces

• 1、 Taniguchi, Tohru,Nakano, Kie,Baba, Ryosuke,Monde, Kenji. "Analysis of Configuration and Conformation of Furanose Ring in Carbohydrate and Nucleoside by Vibrational Circular Dichroism". supporting information. p. 404 - 407. Retrieved 2017/04/21.
• 2、 Wang, Qiang,Li, Yanfeng,Song, Chuanjun,Qian, Keduo,Chen, Chin-Ho,Lee, Kuo-Hsiung,Chang, Junbiao. "Synthesis and anti-HIV activity of 2′-deoxy-2′-fluoro-4′-C-ethynyl nucleoside analogs". supporting information; experimental part. p. 4053 - 4056. Retrieved 2010/08/19.