69123-94-0

Basic information

• Product Name: 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil
• Synonyms: 2’-fluoro-5-ethyl-1-beta-d-arabinofuranosyluracil;1,3-Dimethyl-4-Amino-5-Formamide-Uracil FAU;1-(2'-Deoxy-2'-fluoro-b-D-arabinofuranosyl)uracil;1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione;2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-;2'-Fluoro-arabinofuranosyl-2'-deoxy-uridine;2'-Deoxy-2'-fluoro-beta-D-arabinouridine;2,4(1H,3H)-PyriMidinedione, 1-(2-deoxy-2-fluoro-b-D-arabinofuranosyl)-
• CAS NO: 69123-94-0
• Molecular Formula: C₉H₁₁FN₂O₅
• Molecular Weight: 246.19
• Mol File: 69123-94-0.mol
• Article Data: 45

Chemical Properties

• Melting Point: 162 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• Appearance: Colourless solid
• Density: 1.63 g/cm³
• Refractive Index: 1.587
• Storage Temp.: 2-8°C
• PKA: 9.39±0.10(Predicted)
• CAS DataBase Reference: 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil(69123-94-0)
• EPA Substance Registry System: 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil(69123-94-0)

Safety Data

• Hazardous Substances Data: 69123-94-0(Hazardous Substances Data)

Usage

Chemical Properties

Colourless solid

InChI:InChI=1/C11H15FN2O6/c12-3-1-5-7(16)8(17)9(18)10(20-5)14-4-2-6(15)13-11(14)19/h2,4-5,7-10,16-18H,1,3H2,(H,13,15,19)/t5?,7-,8-,9+,10?/m1/s1

Upstream product

• 157024-77-6 9-<2-deoxy-2-fluoro-3,5-di-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyl>uracil 
• 157024-75-4 9-<3,5-di-O-(tetrahydropyran-2-yl)-β-D-arabinofuranosyl>uracil 
• 351523-07-4 3',5'-di-O-(tetrahydropyran-2-yl)-2,2'-O-cyclouridine 
• 2192-61-2 5',3'-bis-O-trityl-2'-fluoro-2'-deoxyuridine 
• 16731-33-2 1-(3',5'-di-O-trityl-β-D-arabinofuranosyl)uracil 
• 22423-26-3 O-2,2'-cyclo-5-methyluridine 
• 1012080-86-2 5',3'-bis-O-4,4'-dimethoxytrityl-2'-fluoro-2'-deoxyuridine 
• 3736-77-4 2,2'-Anhydrouridine 
• 16731-31-0 2'-oxo-2'-deoxy-uridine 
• 491594-58-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranose 
• 146954-74-7 2'-deoxy-2'-fluoro-5'-O-(4,4'-dimethoxytrityl)uridine 
• 58-96-8 uridine 
• 10212-13-2 3’,5’-O-acetyl-2’-deoxy-2’-fluorouridine 
• 80765-80-6 2-fluoro-2-deoxy-1,3,5-tri-O-benzoyl-α-D-arabinofuranose 

Downstream Products

• 144822-63-9 C₃₀H₂₉FN₂O₇ 
• 1333126-30-9 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil 

Relevant articles and documents

Synthesis method of 2 ’ -fluoro -2 ’ - deoxyuridine and intermediate thereof

The synthesis method of 2 ’ -fluoro -2 ’ - deoxyuridine is novel in synthetic route, simple and convenient to operate, high in yield, good in safety, free of column chromatography and suitable for industrial production. Among them R is a hydroxyl protecting group, most preferably a tetrahydropyranyl group (THP group) as a hydroxyl protecting group. R is a conventional protecting group for the hydroxyl group in the art, and R THP

DDQ mediated regiospecific protection of primary alcohol and deprotection under neutral conditions: Application of new p-methoxy benzyl-pixyl ether as reagent of choice for nucleoside protection

A simple and efficient protocol is described for regiosepecific protection of primary hydroxyl group both in nucleosides and other molecules with p-methoxy-benzyl 2,7-dimethyl pixylether (MBDPE) in presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). Furthermore, swift deprotection of 2, 7-dimethylpixyl (DMPx) is accomplished with DDQ in MeOH. Both procedures are successfully implemented on gram-scale synthesis of modified nucleosides. This protocol offers mild and neutral conditions for selective protection and deprotection of DMPx group while compatible in presence of other conventional protecting groups such as benzoyl, benzyl, THP, TBDPS and acetonide.

Synthesis of new 2′-deoxy-2′-fluoro-4′-azido nucleoside analogues as potent anti-HIV agents

We prepared 1-(4′-azido-2′-deoxy-2′-fluoro-β-d- arabinofuranosyl)cytosine (10) and its hydrochloride salt (11) as potential antiviral agents based on the favorable antiviral profiles of 4′-substituted nucleosides. Compounds 10 and 11 were synthesized from 1,3,5-O-tribenzoyl-2-deoxy-2-fluoro-d-arabinofuranoside in multiple steps, and their structures were unequivocally established by IR, 1H NMR, 13C NMR, and 19F NMR spectroscopy, HRMS, and X-ray crystallography. Compounds 10 and 11 exhibited potent anti-HIV-1 activity (EC50: 0.3 and 0.13 nM, respectively) without significant cytotoxicity in concentrations up to 100 μM. Compound 11 exhibited extremely potent anti-HIV activity against NL4-3 (wild-type), NL4-3 (K101E), and RTMDR viral strains, with EC50 values of 0.086, 0.15, and 0.11 nM, respectively. Due to the high potency of 11, it was also screened against an NIH Reagent Program NRTI-resistant virus panel containing eleven mutated viral strains and for cytotoxicity against six different human cell lines. The results of this screening indicated that 11 is a novel NRTI that could be developed as an anti-AIDS clinical trial candidate to overcome drug-resistance issues.