13089-48-0

Basic information

• Product Name: N-Benzoylcytidine
• Synonyms: N(sup 4)benzoylcytidine;N4-Bz-rC;Bz-rC;NSC 242979;N-(1-(3,4-Dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyriMidin-4-yl)benzaMide;4N-Benzoyl Cytidine;N4-Benzoylcytidine;N-(1-(3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzam
• CAS NO: 13089-48-0
• Molecular Formula: C₁₆H₁₇N₃O₆
• Molecular Weight: 347.32
• EINECS: 2017-001-1
• Product Categories: Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Nucleotides;Nucleosides;Oligonucleotide Synthesis;Specialty Synthesis;Nucleotides and Nucleosides;Biochemistry;Nucleosides and their analogs
• Mol File: 13089-48-0.mol
• Article Data: 31

Chemical Properties

• Melting Point: 230-234 °C (dec.)(lit.)
• Appearance: White to Off-white/Crystalline Powder
• Density: 1.59 g/cm³
• Refractive Index: 46 ° (C=1, DMSO)
• Storage Temp.: Store at 0°C
• Solubility: Soluble in 1N NaOH at 10mg/ml. Also soluble in methanol or DMSO
• PKA: 8.61±0.20(Predicted)
• CAS DataBase Reference: N-Benzoylcytidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzoylcytidine(13089-48-0)
• EPA Substance Registry System: N-Benzoylcytidine(13089-48-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 13089-48-0(Hazardous Substances Data)

Usage

Description

N-Benzoylcytidine is a slightly pink solid that serves as a valuable building block for the synthesis of oligoribonucleotides. It is a modified nucleoside derivative, which plays a crucial role in the development of various applications in the field of molecular biology and pharmaceuticals.

Uses

Used in Oligoribonucleotide Synthesis:
N-Benzoylcytidine is used as a building block for the synthesis of oligoribonucleotides, which are essential in the development of various applications in molecular biology and pharmaceuticals. These oligoribonucleotides can be utilized in the creation of antisense molecules, RNA interference (RNAi) agents, and other therapeutic agents that target specific genes or RNA molecules for the treatment of various diseases.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-Benzoylcytidine is used as a key component in the development of novel drugs and therapeutic agents. Its role in oligoribonucleotide synthesis allows for the creation of targeted treatments for a wide range of diseases, including cancer, genetic disorders, and viral infections.
Used in Molecular Biology Research:
N-Benzoylcytidine is also used in molecular biology research as a tool for studying the structure, function, and interactions of RNA molecules. Its incorporation into oligoribonucleotides enables researchers to investigate the mechanisms of gene regulation, RNA processing, and other cellular processes at the molecular level.

InChI:InChI=1/C16H17N3O6/c20-8-10-12(21)13(22)15(25-10)19-7-6-11(18-16(19)24)17-14(23)9-4-2-1-3-5-9/h1-7,10,12-13,15,20-22H,8H2,(H,17,18,23,24)/t10-,12-,13-,15-/m1/s1

Upstream product

• 39946-94-6 4-N-benzoyl-2',3'-O-isopropylidenecytidine 
• 147490-72-0 4-N-benzoyl-2'-O-<1-(2-fluorophenyl)-4-methoxypiperidin-4-yl>cytidine 
• 118684-37-0 O^2',O^3',O^5'-tris-trimethylsilyl-N⁴-benzoylcytidine 
• 97626-95-4 N⁴-benzoyl-1-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-cytosine 
• 65-85-0 benzoic acid 
• 65-46-3 CYTIDINE 
• 69304-43-4 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N⁴-benzoylcytosine 
• 1314034-30-4 N₄-benzoyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-(methoxymethyl)cytidine 
• 80015-55-0 2'-O-(4-methoxybenzyl)cytidine 
• 98-88-4 benzoyl chloride 
• 263009-01-4 4-N-Benzoyl-2'-O-[1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl]cytidine 
• 93-97-0 benzoic acid anhydride 
• 80015-59-4 2'-O-(4-methoxybenzyl)-N⁴-benzoylcytidine 

Downstream Products

• 28521-72-4 N⁴-benzoyl-O^2'_,O3'-phenylboranediyl-cytidine 
• 52571-45-6 2'-O-methyl-N⁴-benzoylcytidine 
• 99519-17-2 2',3'-diacetyl-N⁴-benzoylcytidine 
• 72409-20-2 N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)cytidine 
• 72429-31-3 N⁴-benzoyl-3',5'-di-O-tert-butyldimethylsilylcytidine 
• 72429-30-2 N⁴-benzoyl-2',5'-di-O-tert-butyldimethylsilylcytidine 
• 77772-57-7 N⁴-benzoyl-2',3'-O-(triphenylphosphoranediyl)-O²,5'-cyclocytidine 
• 104110-05-6 Thiophosphoric acid O-[(2R,3S,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester O',O''-bis-(4-nitro-phenyl) ester 
• 31505-94-9 N-[1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 
• 72687-04-8 Acetic acid (2R,3R,4R,5R)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester 
• 28224-89-7 O^3'-acetyl-N⁴-benzoyl-cytidine 
• 69304-43-4 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N⁴-benzoylcytosine 
• 82434-62-6 N-(1-{(2R,3R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide 
• 82434-58-0 4-N-benzoyl-1-(2,5-O-bis-dimethoxytrityl-β-D-ribofuranosyl)cytosine 

Relevant articles and documents

Microwaves - A powerful tool for the base protection of cytidine

Use of microwaves for the base protection of cytidine is described. The procedure gives N-acylcytidine in nearly quantitative yield in 40-60 seconds.

Synthesis method for azvudine

The invention discloses a synthesis method for azvudine. The method comprises the following steps of carrying out a hydroxyl substitution reaction on a compound 4 and an iodine elementary substance toobtain a compound 5, carrying out an elimination reaction on an iodo group in the compound 5 to obtain a compound 6, reacting the compound 6 with azide under the catalysis of ICl to obtain a compound7, carrying out an iodine substitution reaction on the compound 7 and carboxylic acid to obtain a compound 8, and carrying out an amino and hydroxyl deprotection reaction on the compound 8 to obtaina compound 9, namely the alzvudine. Compared with an existing synthesis method, the synthesis method has the advantages of short synthesis route, shortened reaction time, mild reaction conditions andeasily controlled reaction process, can be used for preparing the alzvudine with the lower cost, and has a very good application prospect.

New tools in nucleoside toolbox of tick-borne encephalitis virus reproduction inhibitors

Design and development of nucleoside analogs is an established strategy in the antiviral drug discovery field. Nevertheless, for many viruses the coverage of structure-activity relationships (SAR) in the nucleoside chemical space is not sufficient. Here we present the nucleoside SAR exploration for tick-borne encephalitis virus (TBEV), a member of Flavivirus genus. Promising antiviral activity may be achieved by introduction of large hydrophobic substituents in the position 6 of adenosine or bulky silyl groups to the position 5′. Introduction of methyls to the ribose moiety does not lead to inhibition of TBEV reproduction. Possible mechanisms of action of these nucleosides include the inhibition of viral entry or interaction with TBEV non-structural protein 5 methyltransferase or RNA-dependent RNA polymerase domains.