178374-44-2

Basic information

• Product Name: 2',3'-Dideoxy-3'-fluoro-a-D-uridine
• Synonyms: 2',3'-Dideoxy-3'-fluoro-a-D-uridine;2',3'-Dideoxy-3'-fluoro-a-uridine;2',3'-Dideoxy-3'-fluoro-alpha-uridine
• CAS NO: 178374-44-2
• Molecular Formula: C9H11FN2O4
• Molecular Weight: 230.1930432
• Mol File: 178374-44-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2',3'-Dideoxy-3'-fluoro-a-D-uridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-Dideoxy-3'-fluoro-a-D-uridine(178374-44-2)
• EPA Substance Registry System: 2',3'-Dideoxy-3'-fluoro-a-D-uridine(178374-44-2)

Safety Data

• Hazardous Substances Data: 178374-44-2(Hazardous Substances Data)

Usage

Uses

2'',3''-Dideoxy-3''-fluoro-alpha-uridine

Upstream product

• 302335-75-7 methyl 5-O-benzoyl-2-deoxy-α/β-L-xylofuranoside 
• 302349-32-2 (2S,3S)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3-ol 
• 73416-11-2 bis-trimethylsilyluracil 
• 302335-76-8 methyl 5-O-benzoyl-2,3-dideoxy-3-fluoro-α/β-L-ribofuranoside 
• 951-78-0 L-Deoxyuridine 
• 207128-18-5 1-((2S,4S,5S)-4-Hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 816429-66-0 5'-O-trityl-2'-deoxy-L-uridine 
• 207128-16-3 Methanesulfonic acid (2S,3R,5S)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 207128-21-0 1-((2S,4R,5S)-4-Fluoro-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 182187-98-0 5'-O-benzoyl-2',3'-dideoxy-3'-fluorouridine 

Downstream Products

• 51247-09-7 5'-O-Acetyl-2',3'-dideoxy-3'-fluorouridine 
• 177365-14-9 β-L-2',3'-dideoxy-3'-fluorocytidine 
• 1277164-77-8 C₃₀H₃₁FN₂O₄Si 
• 119644-23-4 5-iodo-2',3'-dideoxy-3'-fluorouridine 

Relevant articles and documents

Synthesis of 3′-Deoxy-3′-fluoro and -3′-amino Nucleosides from 2-Methylthiopyrimidin-4(1H)-ones

Methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside (3) as well as 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimodo-β-D-erythro-pentofuranose (12) were condensed with silylated 2-methylthiopyridin-4(1H)-ones 2a, b in the presence of trimethylsilyl triflate as a catalyst to produce the corresponding nucleosides 5, 6, 13. In these reactions, an endocyclic cleavage of C-O in 3 took place; therefore, acyclic nucleosides 4a, b were also formed. All 3′-fluoro nucleosides were deprotected with NH3/MeOH; the 3′-phthalimido nucleosides were deprotected with methylamine in ethanol. The latter method resulted in a concomitant substitution reaction in the pyrimidine moiety with replacement of the methylthio group. The 2-methylthio analogue of 3′-deoxy-3′-fluorothylmidine showed moderate activity against HIV-1.

Synthesis of 2',3'-dideoxy-3'-fluoro-L-ribonucleosides as potential antiviral agents from D-sorbitol

2',3'-Dideoxy-3'-fluoro-L-ribonucleosides were synthesized as potential antiviral agents. The key intermediate, methyl 5-O-benzoyl-2-3-dideoxy-3-fluoro-L-ribofuranoside, which was prepared from D-sorbitol, was condensed with pyrimidine and purine bases to obtain the respective nucleosides. Among them, the cytosine analogue 2',3'-dideoxy-3'-fluoro-α-L-cytidine showed a moderate anti-HBV activity. (C) 2000 Elsevier Science Ltd.

Newly synthesized L-enantiomers of 3'-fluoro-modified β-2'- deoxyribonucleoside 5'-triphosphates inhibit hepatitis B DNA polymerases but not the five cellular DNA polymerases α, β, Γ, δ, and ε nor HIV-1 reverse transcriptase

Novel β-L-2',3'-dideoxy-3'-fluoro nucleosides were synthesized and further converted to their 5'-triphosphates. Their inhibitory activities against hepatitis B virus (HBV) and duck hepatitis B virus (DHBV) DNA polymerases, α, ?, γ, δ and ε were investigat

Method of treating HIV infections with 2',3'-dideoxy-3'-fluoro-5-chlorouridine

A method for treating HIV infections comprising administering a composition whose active ingredient is 2',3'-dideoxy-3'-fluoro-5'-chlorouridine.

Antiviral agents

Nucleoside compounds of the formula STR1 wherein: B is a purine or a pyrimidine; X and X' are H, OH or F, provided that at least one is H; Y and Y' are H, OH, OCH3 or F, provided that at least one is H; Y' and Z together form a cyclic phosphate ester, provided that Y is H; or Z is STR2 where n is zero, one, two or three; and Z' is N3 or OCH3 ; provided that when X' and Y' are OH and Z' is N3, B is not cytosine, and when X' and Y' are OH and Z' is OCH3, B is not uracil, adenine or cytosine; and the pharmaceutically acceptable esters, ethers and salts thereof, have been found to have potent antiviral activity with a high therapeutic ratio.

Antiviral compounds

2',3'-Dideoxy-3'-fluoro pyrimidine nucleosides particularly 2',3'-dideoxy-3'-fluorothymidine have been found to have particularly potent activity against adenovirus infections especially those caused by adenoviruses of serotype 8. Such compounds are preferably presented in pharmaceutical formulations adapted for ophthalmic administration.

Fluorinated nucleosides and method for treating retrovirus infections therewith

A method for treating AIDS, which comprises administering to a patient in need therefor a pharmaceutical composition comprising a therapeutically effective amount of a compound having the formula STR1 wherein R 1 is an adenine, cytosine, guanine, thymidine, uracil, 5-substituted uracil, 5-substituted cytosine derivative, 2-fluoroadenine, 2.6-diaminopurine, 2-aminopurine, 6-thioguanine, or 7-deazaadenine group;R 2 is H, or a OH group;R 3 is a OH, O-acyl, O-palmitoyl group, or phosphates (as free acid, or its alkali, ammonium or alkyl ammonium salts), or any other precursor group for the hydroxyl group;or a physiologically acceptable salt thereof. Furthermore, the present invention comprises the new compounds:2'',3''-dideoxy-3''-fluoro-2-fluoroadenosine,2'',3''-dideoxy-3''-fluoro-6-thioguanosine,2'',3''-dideoxy-3''-fluoro-2,6-diaminopurineriboside,2'',3''-dideoxy-3''-fluoro-2-aminopurineriboside,2'',3''-dideoxy-3''-fluoro-5-aminomethyluridine,2'',3''-dideoxy-3''-fluoro-5-azidomethyluridine, and2'',3''-dideoxy-3''-fluoro-5-hydroxymethyluridine.