784-71-4

Basic information

• Product Name: 2'-Fluoro-2'-deoxyuridine
• Synonyms: 1-(2'-FLUORO-2'-DESOXY-BETA-D-RIBOFURANOSYL)URACIL;2,4(1H,3H)-PYRIMIDINEDIONE, 1-(2-DEOXY-2-FLUORO-BETA-D-RIBOFURANOSYL);2'-FLUORO-2'-DEOXYURIDINE;2'-FLUORO-2'-DESOXY-URIDINE;2'-DEOXY-2'-FLUOROURIDINE;2'-FLUORO-D-URIDINE;2'-FUDR;2'-FU
• CAS NO: 784-71-4
• Molecular Formula: C₉H₁₁FN₂O₅
• Molecular Weight: 246.19
• EINECS: 1806241-263-5
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;API intermediates;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 784-71-4.mol
• Article Data: 37

Chemical Properties

• Melting Point: 147.0 to 153.0 °C
• Appearance: White to Off-white/Powder
• Density: 1.63 g/cm³
• Refractive Index: 53 ° (C=0.3, H2O)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Soluble in methanol.
• PKA: 9.39±0.10(Predicted)
• CAS DataBase Reference: 2'-Fluoro-2'-deoxyuridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Fluoro-2'-deoxyuridine(784-71-4)
• EPA Substance Registry System: 2'-Fluoro-2'-deoxyuridine(784-71-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36/37/39
• Hazardous Substances Data: 784-71-4(Hazardous Substances Data)

Usage

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.

Chemical Properties

White to almost white crystalline powder

Uses

Different sources of media describe the Uses of 784-71-4 differently. You can refer to the following data:
1. 2'-Fluoro-2'-deoxyuridine is used as a component incorporated into therapeutic oligonucleotides to combat prostate and breast cancer.
2. A component incorporated into therapeutic oligonucleotides to combat prostate and breast cancer.

Upstream product

• 1012080-86-2 5',3'-bis-O-4,4'-dimethoxytrityl-2'-fluoro-2'-deoxyuridine 
• 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 
• 22423-26-3 O-2,2'-cyclo-5-methyluridine 
• 16731-31-0 2'-oxo-2'-deoxy-uridine 
• 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 
• 3736-77-4 2,2'-Anhydrouridine 
• 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 
• 157024-77-6 9-<2-deoxy-2-fluoro-3,5-di-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyl>uracil 

Downstream Products

• 2923-90-2 5'-O-trityl-2'-deoxy-2'-fluorouridine 
• 146954-74-7 2'-deoxy-2'-fluoro-5'-O-(4,4'-dimethoxytrityl)uridine 
• 55612-21-0 1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione 
• 65-46-3 CYTIDINE 
• 3083-77-0 araU 
• 292037-79-7 O²,2'-anhydro-1-(β-D-arabinofuranosyl)uracil 
• 2192-61-2 5',3'-bis-O-trityl-2'-fluoro-2'-deoxyuridine 

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.

Novel Dideoxynucleoside Derivatives

The present invention discloses a 5′-amino-2′-fluoro-2′,5′-dideoxynucleoside derivative represented by the following formula [1]: (wherein R1 represents a nucleic acid base which may have a protecting group; R2 represents a hydrogen atom or a protecting group of an amino group; R3 represents a hydrogen atom or a protecting group of a hydroxyl group); a dideoxynucleoside-insoluble carrier bound substance prepared by binding said dideoxynucleoside derivative to an insoluble carrier, and an oligonucleotide analogue into which said dideoxynucleoside derivative is introduced. The oligonucleotide analogue being introduced with a dideoxynucleoside derivative of the present invention has excellent thermal stability and also high binding affinity when duplex is formed. Also, it is anticipated that it has high resistance to nucleases. Further, the dideoxynucleoside derivative of the present invention can be used as an amidite reagent to be used for nucleic acid synthesis, and also as a starting material for solid phase synthesis of nucleic acid by binding the amidite reagent to a solid phase.