4836-13-9

Basic information

• Product Name: N-Benzoyl-2'-deoxy-cytidine
• Synonyms: N-[1-(2-Deoxy-β-D-ribofuranosyl)-2-oxo-1,2-dihydropyrimidine-4-yl]benzamide;N-Benzoyl-2'-deoxycytidine, 98+%;bz-dC;N4-Bz-dC;N-Benzoyldeoxycytidine;4-(Benzoylamino)-1-(2-deoxy-beta-L-erythro-pentofuranosyl)-2(1H)-pyrimidinone;DC-N-BZ;DC-BZ
• CAS NO: 4836-13-9
• Molecular Formula: C₁₆H₁₇N₃O₅
• Molecular Weight: 331.32
• EINECS: 225-421-9
• Product Categories: Pyrimidines;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleosides;Oligonucleotide Synthesis;Specialty Synthesis;Building Blocks;Heterocyclic Building Blocks
• Mol File: 4836-13-9.mol
• Article Data: 29

Chemical Properties

• Melting Point: 215-220 °C (dec.)
• Appearance: white to off-white powder
• Density: 1.5 g/cm³
• Refractive Index: 90 ° (C=0.25, MeOH)
• Storage Temp.: −20°C
• Solubility: Soluble in methanol (50 mg/ml).
• PKA: 8.67±0.20(Predicted)
• CAS DataBase Reference: N-Benzoyl-2'-deoxy-cytidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzoyl-2'-deoxy-cytidine(4836-13-9)
• EPA Substance Registry System: N-Benzoyl-2'-deoxy-cytidine(4836-13-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 1-3-10
• Hazardous Substances Data: 4836-13-9(Hazardous Substances Data)

Usage

Uses

Reactant in the synthesis of 2', 5'-Dideoxycytidines and Other Derivatives of 2'-Deoxycytidine, N-Protected 2?-Deoxyribonucleosides(useful for oligonucleotide synthesis), 3?-, 5?-and 3?, 5?-di-O-crotonyl 2?-deoxynucleoside derivatives.

Upstream product

• 3992-42-5 2'-deoxycytidine monohydrochloride 
• 98-88-4 benzoyl chloride 
• 31501-22-1 N⁴-benzoyl-1-(3',5'-di-O-benzoyl-2'-deoxy-β-D-ribofuranosyl)-cytosine 
• 3019-98-5 pentachlorophenyl benzoate 
• 951-77-9 2'-Deoxycytidine 
• 1548-84-1 pentafluorophenyl benzoate 
• 7396-95-4 2,4,5-Trichlorophenyl benzoate 
• 93-97-0 benzoic acid anhydride 
• 51549-38-3 N⁴-benzoyl-O^3',O^5'-bis(tert-butyldimethylsilyl)-2'-deoxycytidine 
• 1336-21-6 ammonium hydroxide 
• 65-85-0 benzoic acid 
• 56632-83-8 1-(2-fluoro-2-deoxy-β-D-arabinofuranosyl)cytosine 
• 51549-29-2 2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine 
• 51432-42-9 4-Amino-1-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one 

Downstream Products

• 81312-43-8 5'-O-monomethoxytrityl-N-benzoyldeoxycytidine 3'-p-chlorophenyl phosphate 
• 75125-22-3 Benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 
• 51549-49-6 N-benzoyl-2'-deoxycytidine 3'-benzoate 
• 177738-37-3 5’-S-acetyl-N-4-benzoyl-3’-O-(4,4-dimethoxytriphenyl)methyl-2’,5’-deoxy-5’-thiocytidine 
• 177738-39-5 N-4-benzoyl-3-O-(4,4-dimethoxytriphenyl)methyl-2,5-dideoxy-5-thiocytidine 
• 170236-48-3 Methanesulfonic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 
• 172161-64-7 5'-S-acetyl-N⁴-benzoyl-2',5'-dideoxy-5'-thiocytidine 
• 22882-02-6 4-methylamino-1-(β-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one 
• 951-77-9 2'-Deoxycytidine 
• 74597-69-6 5'-azido-2',5'-dideoxy-N⁴-benzoylcytidine 
• 60920-99-2 N⁴-Benzoyl-5'-O-monomethoxytrityl-2'-deoxycytidine 
• 139244-40-9 N-(1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 
• 4803-92-3 (5'-O,4-N)-dibenzoyl-2'-deoxycytidine 
• 79527-48-3 C₅₈H₄₇Cl₂N₈O₁₂P 

Relevant articles and documents

Towards Zwitterionic Oligonucleotides with Improved Properties: the NAA/LNA-Gapmer Approach

Oligonucleotides (ON) are promising therapeutic candidates, for instance by blocking endogenous mRNA (antisense mechanism). However, ON usually require structural modifications of the native nucleic acid backbone to ensure satisfying pharmacokinetic properties. One such strategy to design novel antisense oligonucleotides is to replace native phosphate diester units by positively charged artificial linkages, thus leading to (partially) zwitterionic backbone structures. Herein, we report a “gapmer” architecture comprised of one zwitterionic central segment (“gap”) containing nucleosyl amino acid (NAA) modifications and two outer segments of locked nucleic acid (LNA). This NAA/LNA-gapmer approach furnished a partially zwitterionic ON with optimised properties: i) the formation of stable ON-RNA duplexes with base-pairing fidelity and superior target selectivity at 37 °C; and ii) excellent stability in complex biological media. Overall, the NAA/LNA-gapmer approach is thus established as a strategy to design partially zwitterionic ON for the future development of novel antisense agents.

Pyrimidine-purine and pyrimidine heterodinucleosides synthesis containing a triazole linkage

This article describes a synthetic route to generate two purine-pyrimidine and pyrimidine heterodinucleosides. Both microwave activated regioselective alkylation using hydride and copper-catalyzed-azide-alkyne-cycloaddition (CuAAC) were used in order to perform the synthesis.

An efficient one-pot N-acylation of deoxy- and ribo-cytidine using carboxylic acids activated in situ with 2-chloro-4,6-dimethoxy-1,3,5-triazine

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