2'-Deoxy-2'-fluorocytidine

Base Information

• Chemical Name: 2'-Deoxy-2'-fluorocytidine
• CAS No.: 10212-20-1
• Molecular Formula: C9H12FN3O4
• Molecular Weight: 245.21
• Hs Code.: 29389090
• UNII: LCY080JPY9
• Nikkaji Number: J556.916H
• Wikidata: Q27282917
• ChEMBL ID: CHEMBL374528
• Mol file: 10212-20-1.mol

Synonyms:2'-deoxy-2'-fluorocytidine;2'-fluoro-2'-deoxycytidine

Chemical Property of 2'-Deoxy-2'-fluorocytidine

Chemical Property:

• Appearance/Colour: White or almost white crystalline powder
• Melting Point: 167 °C
• Refractive Index: 80 ° (C=1, MeOH)
• Boiling Point: 500.1 °C at 760 mmHg
• PKA: 12.84±0.70(Predicted)
• Flash Point: 256.2 °C
• PSA: 110.60000
• Density: 1.82 g/cm³
• LogP: -1.00460
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO, Methanol.
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 245.08118403
• Heavy Atom Count: 17
• Complexity: 386

Purity/Quality:

98%, ^*data from raw suppliers

2’-Deoxy-2’-fluoroCytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)F
• Isomeric SMILES: C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)F
• Recent ClinicalTrials: Clinical Study to Compare the Efficacy and Safety of Macitentan and Tadalafil Monotherapies With the Corresponding Fixed-dose Combination Therapy in Subjects With Pulmonary Arterial Hypertension (PAH)
• Recent EU Clinical Trials: A Phase 3 Evaluation of a daclatasvir/asunaprevir/BMS-791325 Fixed Dose Combination in Non-cirrhotic Subjects with Genotype 1 Chronic Hepatitis C
• Uses: 2'-Deoxy-2'-fluorocytidine is a potent inhibitor of the subgenomic hepatitis C virus replicon in Huh-7 cells. 2'-Deoxy-2'-fluorocytidine has been shown to inhibit Borna Disease virus replication and s pread. 2'-Fluoro-2'-deoxycytidine is a potent inhibitor of the subgenomic hepatitis C virus replicon in Huh-7 cells. 2'-Fluoro-2'-deoxycytidine has been shown to inhibit Borna Disease virus replication and spread.

Technology Process of 2'-Deoxy-2'-fluorocytidine

There total 14 articles about 2'-Deoxy-2'-fluorocytidine 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: 66.0%

9-<2-deoxy-2-fluoro-3,5-di-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyl>cytosine (157024-78-7) → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Guidance literature:

With ethanol; pyridinium p-toluenesulfonate; for 24h; Heating;

DOI:10.1248/cpb.42.595

Reference yield: 56.0%

3',5'-Di-O-benzoyl-2'-desoxy-2'-fluorcytidin → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Guidance literature:

With ammonium hydroxide; at 50 ℃;

Reference yield:

2'-deoxy-2'-fluorouridine (56287-17-3,69123-94-0,784-71-4) → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / pyridine / 2 h / Ambient temperature

2: (PhO)2POCl, Et₃N / acetonitrile / 1.5 h / Ambient temperature

3: 32percent aq. NH₃ / dioxane / 0.33 h

4: EtNMe₂ / methanol / 24 h / 50 °C

With ammonium hydroxide; N,N-dimethyl-ethanamine; triethylamine; chlorophosphoric acid diphenyl ester; In 1,4-dioxane; pyridine; methanol; acetonitrile;

DOI:10.1002/hlca.19970800614

upstream raw materials:

9-<2-deoxy-2-fluoro-3,5-di-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyl>cytosine

cyclocitidine

3’,5’-O-acetyl-2’-deoxy-2’-fluorouridine

2'-deoxy-2'-fluorouridine

Downstream raw materials:

N4-benzoyl-2-deoxy-2-fluorocytidine

2,6-diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine

5-iodo-2'-deoxy-2'-(R)-fluoro-cytidine

2'-deoxy-2'-fluoroguanosine