2'-Deoxy-2'-fluorouridine

Base Information

• Chemical Name: 2'-Deoxy-2'-fluorouridine
• CAS No.: 784-71-4
• Molecular Formula: C₉H₁₁FN₂O₅
• Molecular Weight: 246.195
• Hs Code.: 29389090
• European Community (EC) Number: 810-296-0
• UNII: Y2YC903QW8
• DSSTox Substance ID: DTXSID50999738
• Nikkaji Number: J338.152H
• Wikidata: Q27294189
• ChEMBL ID: CHEMBL2385615
• Mol file: 784-71-4.mol

Synonyms:2'fluoro-2'-deoxyuridine;2'fluoro-2'-deoxyuridine (2FDU);2FDU

Chemical Property of 2'-Deoxy-2'-fluorouridine

Chemical Property:

• Melting Point: 147.0 to 153.0 °C
• Refractive Index: 53 ° (C=0.3, H2O)
• PKA: 9.39±0.10(Predicted)
• PSA: 104.55000
• Density: 1.63 g/cm³
• LogP: -1.87470
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Soluble in methanol.
• 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:

97% ^*data from raw suppliers

2''-Fluoro-2''-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36/37/39

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
• Description: 2'-Deoxy-2'-fluorouridine is a nucleoside analog that inhibits the replication of wild-type viruses by binding to the viral RNA. 2'-Deoxy-2'-fluorouridine has been shown to inhibit the replication of resistant mutants in vitro, and this inhibition can be reversed by increasing the concentration of 2'-deoxy-2'-fluorouridine. 2'-Deoxy-2'-fluorouridine also binds to duplexes of dsDNA with high affinity and specificity.
• Uses: 2'-Fluoro-2'-deoxyuridine is used as a component incorporated into therapeutic oligonucleotides to combat prostate and breast cancer. A component incorporated into therapeutic oligonucleotides to combat prostate and breast cancer.

Technology Process of 2'-Deoxy-2'-fluorouridine

There total 20 articles about 2'-Deoxy-2'-fluorouridine 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'-fluorodeoxyadenosine

2'-Deoxy-2,2'-difluoro-adenosine

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

Refernces

• 1、 Penjarla, Srishylam,Prasad, S. Rajendra,Reddy, Dhande Sudhakar,Banerjee, Shyamapada,Penta, Santhosh,Sanghvi, Yogesh S.. "Copper(II)nitrate catalyzed regioselective protection of primary alcohols with 4,4′-dimethoxytrityl and 2,7-dimethyl-9-phenyl xanthen-9-yl groups in nucleosides and carbohydrates". . p. 232 - 247. Retrieved 2018/05/14.
• 2、 -. "3-methyl uridine and 4-methyl cytidine nucleoside compound, synthetic method and its pharmaceutical use". Paragraph 0021; 0038. . Retrieved 2016/10/08.