N4-Benzoyl-3'-deoxycytidine

Base Information

• Chemical Name: N4-Benzoyl-3'-deoxycytidine
• CAS No.: 161110-00-5
• Molecular Formula: C16H17N3O5
• Molecular Weight: 331.32
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID80573489
• Wikidata: Q82462226
• Mol file: 161110-00-5.mol

Synonyms:N4-Benzoyl-3'-deoxycytidine;161110-00-5;N-Benzoyl-3'-deoxycytidine;N-[1-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide;Cytidine, N-benzoyl-3'-deoxy- (9CI);N-(1-((2R,3R,5S)-3-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide;Cytidine, N-benzoyl-3'-deoxy-;DTXSID80573489;N-{1-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}benzamide;AKOS015914547;N4-BENZOYL-3/'-DEOXYCYTIDINE;N-[1-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-pyrimidin-4-yl]benzamide

Chemical Property of N4-Benzoyl-3'-deoxycytidine

Chemical Property:

• PKA: 8.65±0.20(Predicted)
• PSA: 113.68000
• Density: 1.503 g/cm³
• LogP: 0.20930
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 331.11682065
• Heavy Atom Count: 24
• Complexity: 556

Purity/Quality:

97% ^*data from raw suppliers

N4-Benzoyl-3''-deoxycytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(C1O)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)CO
• Isomeric SMILES: C1[C@H](O[C@H]([C@@H]1O)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)CO

Technology Process of N4-Benzoyl-3'-deoxycytidine

There total 29 articles about N4-Benzoyl-3'-deoxycytidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

benzoyl chloride (98-88-4) + 3'-deoxycytidine (7057-33-2) → N4-benzoyl-3'-deoxyribicytidine (161110-00-5)

Guidance literature:

3'-deoxycytidine; With chloro-trimethyl-silane; In pyridine; at 20 ℃; for 0.333333h;

benzoyl chloride; In pyridine; at 20 ℃; for 2h;

DOI:10.1081/NCN-100107190

Reference yield: 77.0%

benzoic acid anhydride (93-97-0) + 3'-deoxycytidine (7057-33-2) → N4-benzoyl-3'-deoxyribicytidine (161110-00-5)

Guidance literature:

In methanol; for 4h; Heating;

DOI:10.1080/15257779408012162

Reference yield:

5'-O-trityluridine (6554-10-5) → N4-benzoyl-3'-deoxyribicytidine (161110-00-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 43 percent / DBU / acetonitrile / 15 h / Ambient temperature

2: 65 percent / DMAP / acetonitrile / 20 h / Ambient temperature

3: AIBN, Bu₃SnH / toluene / 3 h / 85 °C

4: TBAF / tetrahydrofuran / 4 h / 75 °C

5: 81 percent / ZnBr₂ / CH₂Cl₂; methanol / 0.33 h

6: 80 percent / pyridine / 20 h / Ambient temperature

7: 69 percent / o-chlorophenylphosphorodichloridate / pyridine / 48 h / Ambient temperature

8: 75 percent / NH₄OH / dioxane / 2.5 h / Ambient temperature

9: 82 percent / NaOEt / 24 h / Ambient temperature

10: 77 percent / methanol / 4 h / Heating

With pyridine; dmap; ammonium hydroxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium ethanolate; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc dibromide; 2-chlorophenyl dichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1080/15257779408012162

upstream raw materials:

benzoic acid anhydride

3'-deoxycytidine

benzoyl chloride

α-D-xylofuranose

Downstream raw materials:

4-N-benzoyl-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine 2-cyanoethyl N,N-diisopropylphosphoramidite

N⁴-benzoyl-5'-O-dimethoxytrityl-3'-deoxyribicytidine

Refernces

• 1、 Rhie,Pfleiderer. "Nucleosides. LVI. Synthesis and chemical modifications of 3'-deoxy- pyrimidine nucleosides". . p. 1425 - 1452. Retrieved 2007/10/02.