Fiacitabine

Base Information

• Chemical Name: Fiacitabine
• CAS No.: 69123-90-6
• Molecular Formula: C9H11FIN3O4
• Molecular Weight: 371.107
• UNII: 4058H365ZB
• DSSTox Substance ID: DTXSID8057807
• Nikkaji Number: J22.241K
• Wikidata: Q27258286
• NCI Thesaurus Code: C73202
• Metabolomics Workbench ID: 153796
• ChEMBL ID: CHEMBL272557
• Mol file: 69123-90-6.mol

Synonyms:1-(2-fluoro-2-deoxy-beta-D-arabinofuranosyl)-5-iodocytosine;2'-deoxy-2'-fluoro-beta-arabinofuranosyl-5-iodocytosine;2'-fluoro-5-iodo-1-beta-D-arabinofuranosylcytosine;2'-fluoro-5-iodo-aracytosine;2(1H)-pyrimidinone, 4-amino-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodo-;4-amino-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodo-2(1H)-pyrimidinone,;FIAC;fiacitabine;fiacitabine monohydrochloride;fiacitabine monohydrochloride, 2-(14)C-labeled;fiacitabine, (alpha-D)-isomer

Chemical Property of Fiacitabine

Chemical Property:

• Vapor Pressure: 3.37E-13mmHg at 25°C
• Refractive Index: 1.791
• Boiling Point: 524.6 °C at 760 mmHg
• PKA: 12.84±0.70(Predicted)
• Flash Point: 271.1 °C
• PSA: 110.60000
• Density: 2.44 g/cm³
• LogP: -0.40000
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 370.97783
• Heavy Atom Count: 18
• Complexity: 430

Purity/Quality:

97% ^*data from raw suppliers

Fiacitabine >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=NC(=O)N1C2C(C(C(O2)CO)O)F)N)I
• Isomeric SMILES: C1=C(C(=NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)F)N)I
• Recent ClinicalTrials: The Safety and Effectiveness of FIAC in the Treatment of Cytomegalovirus (CMV) in Patients With AIDS
• Uses: Antiviral. Fiacitabine is an antiviral compound and a selective inhibitior of DNA replication of herpes simplex virus(HSV).

Technology Process of Fiacitabine

There total 10 articles about Fiacitabine 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: 65.0%

1-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-D-arabinofuranosyl)-5-iodocytosine → fiacitabine (69123-90-6)

Guidance literature:

With methanol; ammonia; at 20 ℃; for 48h; Saturated gas;

DOI:10.1016/j.tet.2012.04.031

Reference yield:

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → fiacitabine (69123-90-6)

Guidance literature:

Multi-step reaction with 5 steps

1: diethylamino-sulfur trifluoride

2: hydrogen bromide; acetic acid

3: 1,2-dichloro-ethane / 48 h / 20 °C / Inert atmosphere

4: methanol / dichloromethane; 1,2-dichloro-ethane

5: methanol; ammonia / 48 h / 20 °C / Saturated gas

With methanol; diethylamino-sulfur trifluoride; ammonia; hydrogen bromide; acetic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/j.tet.2012.04.031

Reference yield:

1-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-5-iodocytosine (1382358-19-1) → fiacitabine (69123-90-6)

Guidance literature:

With methanol; ammonia; at 20 ℃; for 48h; Saturated gas;

DOI:10.1016/j.tet.2012.04.031

upstream raw materials:

1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodocytosine

1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide

1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose

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

Downstream raw materials:

1-(2-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)-5-iodocytosine

1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5(E)-<2-(ethoxycarbonyl)vinyl>cytosine

1-(2-fluoro-2-deoxy-β-D-arabinofuranosyl)cytosine

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