146954-74-7

Basic information

• Product Name: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-FLUORO-D-URIDINE
• Synonyms: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-FLUORO-D-URIDINE;2'-Deoxy-5'-O-DMT-2'-fluoro-D-uridine;2'-Deoxy-5'-O-DMT-2'-fluorouridine;5'-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-2'-deoxy-2'-fluorouridine;DMT-2'-F-dU;5'-O-(4,4'-DiMethoxytrityl)-2'-fluoro-2'-deoxyuridine;1-((2R,3R,4R,5R)-5-((Bis(4-Methoxyphenyl)(phenyl)Methoxy)Methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione;5'-O-DMT-2'-Fluoro-2'-deoxyuridine
• CAS NO: 146954-74-7
• Molecular Formula: C₃₀H₂₉FN₂O₇
• Molecular Weight: 548.56
• EINECS: 2017-001-1
• Mol File: 146954-74-7.mol

Chemical Properties

• Appearance: White to Pale Yellow/Powder
• Density: 1.38 g/cm³
• Storage Temp.: 2-8°C
• PKA: 9.39±0.10(Predicted)
• CAS DataBase Reference: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-FLUORO-D-URIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-FLUORO-D-URIDINE(146954-74-7)
• EPA Substance Registry System: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-FLUORO-D-URIDINE(146954-74-7)

Safety Data

• Hazardous Substances Data: 146954-74-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry and Biochemistry:
5'-O-(4,4'-DIMETHOXYTRITYL)-2'-FLUORO-D-URIDINE is used as a building block for the synthesis of various nucleoside analogs and nucleic acid-based drugs, due to its 2'-fluoro modification that improves the stability and binding affinity of nucleic acid structures.
Used in Modified RNA Molecule Production:
In the field of RNA research and therapeutics, 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-FLUORO-D-URIDINE is used as a key component in the production of modified RNA molecules, contributing to the development of novel RNA-based therapies and diagnostic tools.
Used in Antiviral Drug Development:
5'-O-(4,4'-DIMETHOXYTRITYL)-2'-FLUORO-D-URIDINE may have potential applications in antiviral drug development, as its unique chemical properties could be harnessed to create new antiviral agents with improved efficacy and selectivity.
Used in Nucleic Acid-based Diagnostics:
5'-O-(4,4'-DIMETHOXYTRITYL)-2'-FLUORO-D-URIDINE may also find use in the development of nucleic acid-based diagnostic tools, where its 2'-fluoro modification could enhance the specificity and sensitivity of diagnostic assays, aiding in the early detection and monitoring of various diseases.

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 56287-17-3 2'-deoxy-2'-fluorouridine 
• 100-66-3 methoxybenzene 
• 98-07-7 Benzotrichlorid 
• 622785-69-7 1-((2S,3S,4S,5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 

Downstream Products

• 146954-75-8 5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-fluorouridine-3'-O-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite] 
• 136671-61-9 (2R,3S,4S,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluorotetrahydrofuran-3-yl methyl diisopropylphosphoramidite 
• 1001648-90-3 C₄₃H₅₅FN₃O₉PS 

Relevant articles and documents

4'-HALOGEN CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

Disclosed are halogen containing nucleotide and nucleoside therapeutic compositions and uses related thereto. In certain embodiments, the disclosure relates to the treatment or prophylaxis of viral infections. Such viral infections can include tongaviridae, bunyaviridae, arenaviridae, coronaviridae, flaviviridae, picornaviridae, Eastern, Western, and Venezuelan Equine Encephalitis (EEE, WEE and VEE, respectively), Chikungunya fever (CHIK), Ebola, Influenza, RSV, and Zika virus infections.

4'-HALOGEN CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

Disclosed are halogen containing nucleotide and nucleoside therapeutic compositions and uses related thereto. In certain embodiments, the disclosure relates to the treatment or prophylaxis of viral infections. Such viral infections can include tongaviridae, bunyaviridae, arenaviridae, coronaviridae, flaviviridae, picornaviridae, Eastern, Western, and Venezuelan Equine Encephalitis (EEE, WEE and VEE, respectively), Chikungunya fever (CHIK), Ebola, Influenza, RSV, and Zika virus infections.

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

Regioselective protection of primary hydroxyl group in nucleoside and carbohydrate analogs was accomplished using dimethoxytrityl alcohol (DMTr-OH) or dimethylpixyl alcohol (DMPx-OH) in presence of copper(II)nitrate as a Lewis acid catalyst. Excellent selectivity was observed for the protection of primary hydroxyl group over secondary while glycosidic bond remain unaffected. Utility of this methodology was further exemplified via DMTr- and DMPx-protection of alipahtic acyclic and cyclic diols.

NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

ALKYNE CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

Anti-flavivirus Activity of Different Tritylated Pyrimidine and Purine Nucleoside Analogues

A series of tritylated and dimethoxytritylated analogues of selected pyrimidine and purine nucleosides were synthesized and evaluated for their in vitro inhibitory activity against two important members of the genus Flavivirus in the Flaviviridae family, the yellow fever (YFV) and dengue viruses (DENV). Among all compounds tested, the 5′-O-tritylated and the 5′-O-dimethoxytritylated 5-fluorouridine derivatives exerted potency against YFV. Interestingly in the series of purine analogues, the 5′O, N-bis-tritylated fludarabine derivative revealed strong inhibitory activity against DENV at μm concentrations, however significantly weaker potency against YFV.

Oligonucleotide with protected base

The present invention provides a protected nucleotide for elongation, which can be purified efficiently and in a high yield by a liquid-liquid extraction operation, and can achieve an oligonucleotide production method by a phosphoramidite method. It has been found that the above-mentioned problem can be solved by a particular oligonucleotide comprising a protected base and/or particular oligonucleotide protected by a branched chain-containing aromatic group at 3′-position.

NUCLEOTIDE AND NUCLEOSIDE THERAPEUTICS COMPOSITIONS AND USES RELATED THERETO

This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

Discovery of 4′-chloromethyl-2′-deoxy-3′,5′-di- O -isobutyryl-2′-fluorocytidine (ALS-8176), A first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection

Respiratory syncytial virus (RSV) is a leading pathogen of childhood and is associated with significant morbidity and mortality. To date, ribavirin is the only approved small molecule drug, which has limited use. The only other RSV drug is palivizumab, a monoclonal antibody, which is used for RSV prophylaxis. Clearly, there is an urgent need for small molecule RSV drugs. This article reports the design, synthesis, anti-RSV activity, metabolism, and pharmacokinetics of a series of 4′-substituted cytidine nucleosides. Among tested compounds 4′-chloromethyl-2′-deoxy-2′-fluorocytidine (2c) exhibited the most promising activity in the RSV replicon assay with an EC50 of 0.15 μM. The 5′-triphosphate of 2c (2c-TP) inhibited RSV polymerase with an IC50 of 0.02 μM without appreciable inhibition of human DNA and RNA polymerases at 100 μM. ALS-8176 (71), the 3′,5′-di-O-isobutyryl prodrug of 2c, demonstrated good oral bioavailability and a high level of 2c-TP in vivo. Compound 71 is a first-in-class nucleoside RSV polymerase inhibitor that demonstrated excellent anti-RSV efficacy and safety in a phase 2 clinical RSV challenge study.