1-(2-Deoxy-2-fluoro-b-D-arabinofuranosyl)uracil

Base Information

• Chemical Name: 1-(2-Deoxy-2-fluoro-b-D-arabinofuranosyl)uracil
• CAS No.: 69123-94-0
• Molecular Formula: C9H11FN2O5
• Molecular Weight: 246.195
• Hs Code.: 2934999090
• UNII: K7386OMP29
• DSSTox Substance ID: DTXSID20219192
• Nikkaji Number: J61.758J
• Wikidata: Q27282035
• NCI Thesaurus Code: C80036
• Metabolomics Workbench ID: 153907
• ChEMBL ID: CHEMBL3228489
• Mol file: 69123-94-0.mol

Synonyms:2'-fluoro-5-ethyl-1-beta-D-ara U;2'-fluoro-5-ethyl-1-beta-D-arabinofuranosyluracil;2'-fluoro-5-ethylarabinosyluracil;FEAU

Chemical Property of 1-(2-Deoxy-2-fluoro-b-D-arabinofuranosyl)uracil

Chemical Property:

• Appearance/Colour: Colourless solid
• Melting Point: 162 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• Refractive Index: 1.587
• PKA: 9.39±0.10(Predicted)
• PSA: 104.55000
• Density: 1.63 g/cm³
• LogP: -1.87470
• Storage Temp.: 2-8°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 246.06519962
• Heavy Atom Count: 17
• Complexity: 374

Purity/Quality:

98%min ^*data from raw suppliers

1-(2-Deoxy-2-fluoro-b-D-arabinofuranosyl)uracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)F
• Isomeric SMILES: C1=CN(C(=O)NC1=O)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)F
• Recent ClinicalTrials: FAU in Treating Patients With Advanced Solid Tumors or Lymphoma

Technology Process of 1-(2-Deoxy-2-fluoro-b-D-arabinofuranosyl)uracil

There total 31 articles about 1-(2-Deoxy-2-fluoro-b-D-arabinofuranosyl)uracil 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: 93.9%

3’,5’-O-acetyl-2’-deoxy-2’-fluorouridine (10212-13-2) → 2'-deoxy-2'-fluorouridine (56287-17-3,69123-94-0,784-71-4)

Guidance literature:

With hydrogenchloride; methanol; water; at 45 - 60 ℃; for 20h; Product distribution / selectivity;

Reference yield: 93.0%

2'-deoxy-2'-fluoro-5'-O-(4,4'-dimethoxytrityl)uridine (146954-74-7) → 2'-deoxy-2'-fluorouridine (56287-17-3,69123-94-0,784-71-4)

Guidance literature:

With copper(II) nitrate; In methanol; at 20 ℃; for 0.25h;

DOI:10.1080/15257770.2018.1460480

Reference yield: 91.0%

C30H27FN2O6 → 2'-deoxy-2'-fluorouridine (56287-17-3,69123-94-0,784-71-4)

Guidance literature:

With methanol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; at 20 ℃; for 0.666667h;

DOI:10.1016/j.tetlet.2017.05.066

upstream raw materials:

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

1-(3',5'-di-O-trityl-β-D-arabinofuranosyl)uracil

5',3'-bis-O-trityl-2'-fluoro-2'-deoxyuridine

2,2'-Anhydrouridine

Downstream raw materials:

5'-O-trityl-2'-deoxy-2'-fluorouridine

2-amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine

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

2'-deoxy-2'-fluoro-5'-O-(4,4'-dimethoxytrityl)uridine