2',3'-Dideoxy-3'-fluorouridine

Base Information

• Chemical Name: 2',3'-Dideoxy-3'-fluorouridine
• CAS No.: 41107-56-6
• Molecular Formula: C9H11 F N2 O4
• Molecular Weight: 230.193
• Hs Code.: 29349990
• European Community (EC) Number: 415-360-8,637-011-0
• DSSTox Substance ID: DTXSID901034059
• Nikkaji Number: J400.565A
• Wikidata: Q82919920
• ChEMBL ID: CHEMBL244975
• Mol file: 41107-56-6.mol

Synonyms:3'-fluoro-2',3'-dideoxyuridine;FDDUrd

Chemical Property of 2',3'-Dideoxy-3'-fluorouridine

Chemical Property:

• Appearance/Colour: Off-white solid
• Melting Point: 184-188 °C(lit.)
• Boiling Point: °Cat760mmHg
• PKA: 9.39±0.10(Predicted)
• Flash Point: °C
• PSA: 84.32000
• Density: 1.5 g/cm³
• LogP: -0.84550
• Storage Temp.: -20°C Freezer
• Solubility.: Aqueous Base (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly), Water
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 230.07028500
• Heavy Atom Count: 16
• Complexity: 346

Purity/Quality:

99.9% ^*data from raw suppliers

2'',3''-Dideoxy-3''-fluorouridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 68
• Safety Statements: 22-36/37

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(OC1N2C=CC(=O)NC2=O)CO)F
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)F
• Uses: 2'',3''-Dideoxy-3''-fluorouridine is a reactant used in the synthesis of 5''-trityl nucleosides as inhibitors of Plasmodium falciparum dUTPase. 2′,3′-Dideoxy-3′-fluorouridine can be used as a starting material in the synthesis of: 3′-fluoro 2′,3′-dideoxynucleoside analogs for in vitro antiviral activity studies. 3′-fluoro deoxyuridine monophosphate analogs as potential anti parasites.

Technology Process of 2',3'-Dideoxy-3'-fluorouridine

There total 3 articles about 2',3'-Dideoxy-3'-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: 30.0%

5'-O-benzoyl-2',3'-dideoxy-3'-fluorouridine (182187-98-0) → 1-(2,3-Dideoxy-3-fluoro-β-D-ribofuranosyl)-uracil (41107-56-6,178374-44-2)

Guidance literature:

With sodium methylate; In methanol;

Reference yield: 23.0%

Biphenyl-4-carboxylic acid (2R,3S,5R)-3-fluoro-5-(2-methylsulfanyl-4-oxo-4H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester → 1-(2,3-Dideoxy-3-fluoro-β-D-ribofuranosyl)-uracil (41107-56-6,178374-44-2)

Guidance literature:

With ammonia; In methanol; for 1h; Ambient temperature;

DOI:10.1007/BF00807039

Reference yield:

→ 2',3'-Didesoxy-3'-fluor-uridin (41107-56-6)

Guidance literature:

2,3'-Anhydro-1-(2-desoxy-5-O-mesyl-β-D-xylo-furanosyl)-uracil, NaOH;

upstream raw materials:

5'-O-benzoyl-2',3'-dideoxy-3'-fluorouridine

Downstream raw materials:

C₃₀H₃₁FN₂O₄Si

5-iodo-2',3'-dideoxy-3'-fluorouridine

2',3'-dideoxy-3'-fluoro-5'-O-(triphenylmethyl)uridine

5'-O-Acetyl-2',3'-dideoxy-3'-fluorouridine

Refernces

• 1、 Janta-Lipinski, Martin von,Langen, Peter,Cech, Dieter. "Zur Spaltung von 2,3'-Anhydronucleosiden mit Halogenwasserstoffsaeuren". . p. 335. Retrieved 2007/10/02.