7057-33-2

Usage

Uses

Used in Antiviral Applications:
3'-Deoxycytidine is used as an antiviral agent for its inhibitory properties against the replication of certain viruses, specifically the hepatitis C virus-like RNA template. By targeting nucleolar RNA synthesis without affecting mRNA appearance, it can help control viral replication and potentially contribute to the development of antiviral therapies.
Used in Molecular Biology Research:
In the field of molecular biology, 3'-Deoxycytidine can be used as a research tool to study the effects of nucleoside modifications on various cellular processes, such as DNA replication, transcription, and RNA processing. Understanding the role of 3'-Deoxycytidine in these processes can provide insights into the molecular mechanisms underlying various diseases and the development of novel therapeutic strategies.
Used in Drug Development:
3'-Deoxycytidine may also be utilized in the development of new drugs targeting specific viral or cellular pathways. Its unique structure and function can be exploited to design molecules with enhanced specificity and efficacy, potentially leading to the creation of more effective treatments for various diseases, including viral infections and cancer.

Upstream product

• 75489-85-9 1-O-acetyl-2,5-di-O-p-chlorobenzoyl-3-deoxy-D-ribofuranose 
• 23583-55-3 1-(2-O-acetyl3,5-O-dibenzoyl-β-D-ribofuranosyl)-4-methoxy-2-pyrimidone 
• 22224-42-6 α-D-2-O-acetyl-1,3,5-tri-O-benzoylribofuranoside 
• 303041-55-6 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2-pyrimidone 
• 216683-07-7 1-((2R,3R,5S)-3-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(4-nitro-phenoxy)-1H-pyrimidin-2-one 
• 173601-08-6 2',5'-di-O-p-chlorobenzoyl-N⁴-propionyl-3'-deoxycytidine 
• 159217-63-7 2'-O-Acetyl-5'-O-benzoyl-4-N-isobutyryl-3'-deoxycytidine 
• 161109-94-0 N⁴,2'-di-N,O-acetyl-3'-deoxy-5'-O-(4-methylbenzoyl)-cytidine 
• 161110-11-8 2',5'-di-O-acetyl-3'-deoxycytidine 
• 75489-86-0 N₄-acetyl-2',5'-di-O-p-chlorobenzoyl-3'-deoxycytidine 
• 114827-12-2 N⁴,O^2',O^5'-tripivaloyl-3'-O-mesylcytidine 
• 130860-13-8 5'-O-trityl-3'-deoxycytidine 
• 52482-85-6 2',5'-di-O-acetyl-3-deoxy-N⁴-acetylcytidine 
• 52482-84-5 N⁴-acetyl-1-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)cytosine 

Downstream Products

• 157327-96-3 4-N-benzoyl-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine 2-cyanoethyl N,N-diisopropylphosphoramidite 
• 86234-45-9 N⁴-benzoyl-5'-O-dimethoxytrityl-3'-deoxyribicytidine 
• 15386-69-3 (2R,3R,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol 
• 114827-16-6 N⁴-(4,4'-dimethoxytrityl)-3'-deoxycytidine 
• 161110-00-5 N⁴-benzoyl-3'-deoxyribicytidine 
• 161110-15-2 N⁴-2-(4-nitrophenyl)ethoxycarbonyl-3'-deoxycytidi 
• 69383-05-7 3'-dCTP 
• 159217-65-9 4-(N-Isobutyryl)-5'-O-(4,4'-dimethoxytrityl)-3'-deoxycytidine 
• 69199-40-2 3'-dUTP 

Relevant academic research and scientific papers

Phosphorus pentachloride promoted gem-dichlorination of 2′- and 3′-deoxynucleosides

Halogen substitution at various positions of canonical nucleosides has generated a number of bioactive structural variants. Herein, the synthesis of two unique series of sugar modified nucleosides bearing a gem-dichloro group is presented. The synthetic plan entails the controlled addition of phosphorus pentachloride to suitably protected 2′- or 3′-ketodeoxynucleoside intermediates as the key step, facilitating the rapid construction of such functionalized molecules. Under the same reaction conditions, the highest chemoselectivity was observed for the formation of 2′,2′-dichloro-2′,3′-dideoxynucleosides, while a competing 2′,3′-elimination process occurred in the case of the 3′,3′-dichloro counterparts.

Preparation method of 3'-deoxyuridine

The invention relates to the field of pharmaceutical synthesis and particularly relates to a preparation method of 3'-deoxyuridine. The method comprises the steps: by adopting a compound 3 as a raw material, firstly protecting amino through acetic anhydride to obtain a compound 4, obtaining a compound 5 under the action of acetyl bromide, reducing through a hypophosphite system to obtain a compound 6; removing deacetylated amino under the action of high-pressure water vapor and an organic solvent to obtain a compound 8 or removing N-acetyl to obtain a compound 7; and finally removing all acetyl to obtain a mixture of 3'-deoxyuridine and 3'-deoxycytidine; separating and purifying to obtain 3'-deoxyuridine crystal and 3'-deoxycytidine crystal separately, or directly removing all acetyl through the compound 6 to obtain the 3'-deoxycytidine. Available natural products are taken as initial raw materials, so that the method is simple in operation and convenient to purify, and industrial large-scale production is extremely easy to implement.

Deoxygenation of 5-O-benzoyl-1,2-isopropylidene-3-O-imidazolylthiocarbonyl-α-d-xylofuranose using dimethyl phosphite: an efficient alternate method towards a 3′-deoxynucleoside glycosyl donor

An efficient radical deoxygenation reaction of thiocarbonylimidazolyl activated glycoside analogue using dimethyl phosphite as hydrogen source and radical chain carrier was performed as a key step in a multi step synthesis towards a common 3-deoxy glycosyl donor for 3′-deoxynucleosides. This method has safety and cost advantages compared to the generally used radical reduction reagents.

Anti-HCV nucleoside derivatives

The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

Modified nucleosides for the treatment of viral infections and abnormal cellular proliferation

The disclosed invention is a composition for and a method of treating a Flaviviridae (including BVDV and HCV), Orthomyxoviridae (including Influenza A and B) or Paramyxoviridae (including RSV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans, using a nucleoside of general formula (I)-(XXIII) or its pharmaceutically acceptable salt or prodrug. This invention also provides an effective process to quantify the viral load, and in particular BVDV, HCV or West Nile Virus load, in a host, using real-time polymerase chain reaction (""RT-PCR""). Additionally, the invention discloses probe molecules that can fluoresce proportionally to the amount of virus present in a sample.

Stereocontrolled Syntheses of Deoxyribonucleosides via Photoinduced Electron-Transfer Deoxygenation of Benzoyl-Protected Ribo- and Arabinonucleosides

The stereocontrolled, de novo syntheses of β-2′-deoxy-, α-2′-deoxy-, β-3′-deoxy-, and β-2′,3′-dideoxyribonucleosides are described. Strategically protected ribose, arabinose, and xylose glycosylation precursors were synthesized bearing C2-esters capable of directing Vorbrueggen glycosylation. The key step is the regioselective deoxygenation of the desired hydroxyl group as either the benzoyl- or 3-(trifluoromethyl)benzoyl derivative. This deoxygenation is accomplished via a photoinduced electron-transfer (PET) mechanism using carbazole derivatives as the photosensitizer. The syntheses of the desired deoxynucleoside generally proceed in three steps from a common, readily available precursor.

2′,3′-Anhydrouridine. A useful synthetic intermediate

2,2′-Anhydro-1-(β-D-arabinofuranosyl)uracil 1 reacts with sodium hydride in dry DMSO to give 2′,3′-anhydrouridine 2. When the latter compound 2 is heated below its melting point or treated with triethylamine in methanol, it isomerises back to the 2,2′-anhydronucleoside 1. Treatment of compound 1 with sodium ethanethiolate or the sodium salt of benzyl mercaptan in the presence of an excess of the corresponding thiol in DMA gives 2′-S-ethyl-or 2′-S-benzyl-2′-thiouridine (4 or 11) in high yield; however, treatment of the 2,2′-anhydronucleoside 1 first with sodium hydride in DMA and then with a deficiency (with respect to sodium hydride) of ethanethiol or benzyl mercaptan gives the corresponding 3′-S-ethyl or 3′-S-benzyl derivative (3 or 12) in high yield. When the 2,2′-anhydronucleoside 1 is allowed to react with an excess of potassium tert-butoxide in DMSO, the 3′,5′-anhydronucleoside 13 is obtained in good yield. The latter compound 13 undergoes hydrolysis in aqueous trifluoroacetic acid to give 1-(β-D-xylofuranosyl)uracil 14 in high yield. The 3′-S-benzyl derivative 12 is converted by Raney nickel desulfurisation into 3′-deoxyuridine 15 which, in turn, is converted into 3′-deoxycytidine 17 in good yield. X-Ray crystallographic data relating to compounds 11 and 12 are also reported.

Synthetic nucleosides and nucleotides. XXXV. Synthesis and biological evaluations of 5-fluoropyrimidine nucleosides and nucleotides of 3-deoxy-β- D-ribofuranose and related compounds

1-O-Acetyl-2,5-di-O-p-chlorobenzoyl-3-deoxy-D-ribofuranose (1), derived from the antibiotic cordycepin was coupled with trimethylsilylated derivatives (2a-c) of N4-propionylcytosine, N4-p-toluoyl-5-fluorocytosine and 5-fluorouracil i

Nucleosides. LVI. Synthesis and chemical modifications of 3'-deoxy- pyrimidine nucleosides

3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O- toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert- butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterized by elemental analyses and UV and 1H-NMR spectra.

Preparation of 2'-O-(β-Cyanoethyl phosphoramidites) of 3'-Deoxycytidine and 3'-Deoxyguanosine and Their Use for Solid-Phase Synthesis of Oligodeoxynucleotides Containing 2',5'-Phosphodiester Linkages

Convenient, preparative scale synthetic routes to 2'-O-(β-cyanoethyl N,N-diisopropylphosphoramidites) of 3'-deoxycytidine (1) and 3'-deoxyguanosine (2) are described.The 3'-deoxycytidine nucleoside 5 was constructed by a modified Hilbert-Johnson reaction in which N-(4-isobutyryl)cytosine (4) was ribosylated with anomeric acetate 3.Nucleoside 5 was converted to 5'-O-(dimethoxytrityl)-4-N-isobutyryl-3'-deoxycytidine (7) and phosphitylated to provide phosphoramidite 1.Access to derivatives of 3'-deoxyguanosine was provided by selective removal of the 3'-hydroxyl of guanosine (10).Thus, the 3'-O-thiocarbamate of 5'-O-(dimethoxytrityl)-2-N-(dimethylformamidyl)-2'-O-(triisopropylsilyl)guanosine (12) was reduced with tributyltin hydride and converted to phosphoramidite 2.In results to be reported elsewhere, phosphoramidites 1 and 2 were used to prepare oligodeoxynucleotides containing novel 2',5'-phosphodiester linkages using automated solid-phase DNA synthesis methods with average stepwise coupling yields of >97percent.