7057-33-2

Basic information

• Product Name: 3'-DEOXYCYTIDINE
• Synonyms: 3’-deoxy-cytidin;3'-DEOXYCYTIDINE;3'-deoxycytidine free base;3'-Deoxy-D-cytidine;3''-Deoxycytidine (and/or unspecified salts);1-(3-Deoxy-β-D-erythro-pentofuranosyl)cytosine;4-amino-1-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;4-amino-1-[(2R,3R,5S)-3-hydroxy-5-methylol-tetrahydrofuran-2-yl]pyrimidin-2-one
• CAS NO: 7057-33-2
• Molecular Formula: C₉H₁₃N₃O₄
• Molecular Weight: 227.22
• Mol File: 7057-33-2.mol
• Article Data: 15

Chemical Properties

• Melting Point: 230-232 °C
• Boiling Point: 497.6 °C at 760 mmHg
• Flash Point: 254.8 °C
• Appearance: /
• Density: 1.73 g/cm³
• Storage Temp.: 2-8°C
• PKA: 14.01±0.60(Predicted)
• CAS DataBase Reference: 3'-DEOXYCYTIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-DEOXYCYTIDINE(7057-33-2)
• EPA Substance Registry System: 3'-DEOXYCYTIDINE(7057-33-2)

Safety Data

• RTECS: HA3830000
• Hazardous Substances Data: 7057-33-2(Hazardous Substances Data)

Usage

Uses

3''-Deoxycytidine is an inhibitor of nucleolar RNA synthesis but does not affect the appearance of mRNA. Displayed inhibitory properties against the replication of hepatitis C virus-like RNA template.

Upstream product

• 161110-11-8 2',5'-di-O-acetyl-3'-deoxycytidine 
• 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 
• 3768-18-1 N-acetylcytidine 
• 65-46-3 CYTIDINE 
• 14631-20-0 4-N-Acetylcytosine 
• 4613-71-2 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose 
• 84017-56-1 N₆,N₆,2',5'-tetra-p-chlorobenzoylcordycepin 
• 75489-85-9 1-O-acetyl-2,5-di-O-p-chlorobenzoyl-3-deoxy-D-ribofuranose 
• 54925-66-5 2',5'-bis-O-(tert-butyldimethylsilyl)uridine 
• 19312-45-9 2',5'-di-O-acetyl-3'-deoxyuridine 
• 161109-93-9 3'-O-phenoxythiocarbonyl-2'-O-thexyldimethylsilyl-5'-O-trityluridine 
• 161109-82-6 2'-O-thexyldimethylsilyl-5'-O-trityluridine 

Downstream Products

• 69199-40-2 3'-dUTP 
• 159217-65-9 4-(N-Isobutyryl)-5'-O-(4,4'-dimethoxytrityl)-3'-deoxycytidine 
• 69383-05-7 3'-dCTP 
• 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 

Relevant articles and documents

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.

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.

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.