Cytochlor

Base Information

• Chemical Name: Cytochlor
• CAS No.: 32387-56-7
• Molecular Formula: C₉H₁₂ClN₃O₄
• Molecular Weight: 261.665
• UNII: J14D49ZN55
• DSSTox Substance ID: DTXSID40186099
• Nikkaji Number: J1.228.514K
• Wikidata: Q27281010
• NCI Thesaurus Code: C28950
• Metabolomics Workbench ID: 153378
• ChEMBL ID: CHEMBL4297275
• Mol file: 32387-56-7.mol

Synonyms:2'-deoxy-5-chlorocytidine;5-chloro-2'-deoxycytidine;5-chlorodeoxycytidine

Chemical Property of Cytochlor

Chemical Property:

• Boiling Point: 497.9°Cat760mmHg
• Flash Point: 254.9°C
• PSA: 110.60000
• Density: 1.86g/cm³
• LogP: -0.29920
• Storage Temp.: 2-8°C
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 261.0516336
• Heavy Atom Count: 17
• Complexity: 398

Purity/Quality:

99% ^*data from raw suppliers

Cytochlor ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=NC2=O)N)Cl)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=NC2=O)N)Cl)CO)O
• Recent ClinicalTrials: Cytochlor and Tetrahydrouridine as Radiosensitizers and Cisplatin Combined With Radiation Therapy in Treating Patients With Advanced Squamous Cell Carcinoma of the Oral Cavity (Mouth) or Oropharynx (Throat)
• Uses: 5-Chloro-2’-deoxycytidine is a good markers to detect myeloperoxidase (MPO) activity in biological fluids. Possible radiosensitizing agent for cancer treatment.

Technology Process of Cytochlor

There total 1 articles about Cytochlor 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: 84.0%

2'-Deoxycytidine (951-77-9) → 5-chloro-2′-deoxycytidine (32387-56-7)

Guidance literature:

With N-chloro-succinimide; 1-ethylene glycol monomethyl ether-3-methylimidazolium methanesulfonate; at 50 ℃; for 1h;

DOI:10.1055/s-0029-1217042

Reference yield:

5-chloro-2′-deoxycytidine (32387-56-7) → 4-N-acetyl-5-chloro-5'-O-(4,4'-dimethoxytrityl)-deoxycytidine (1356140-66-3)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl-formamide / 9 h / 45 °C

2: pyridine / 5 h / 20 °C

With pyridine; In N,N-dimethyl-formamide;

DOI:10.1039/c1ob06411h

Reference yield:

5-chloro-2′-deoxycytidine (32387-56-7) → 4-N-acetyl-5-chloro-5'-O-(4,4'-dimethoxytrityl)-deoxycytidine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) (1356140-67-4)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N-dimethyl-formamide / 9 h / 45 °C

2: pyridine / 5 h / 20 °C

3: 1H-tetrazole; diisopropylamine / dichloromethane / 5 h / 20 °C / Inert atmosphere

With pyridine; 1H-tetrazole; diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c1ob06411h

upstream raw materials:

2'-Deoxycytidine

Downstream raw materials:

4-N-acetyl-5-chloro-5'-O-(4,4'-dimethoxytrityl)-deoxycytidine

4-N-acetyl-5-chloro-5'-O-(4,4'-dimethoxytrityl)-deoxycytidine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite)

Refernces

• 1、 Kanamori, Takashi,Masaki, Yoshiaki,Mizuta, Masahiro,Tsunoda, Hirosuke,Ohkubo, Akihiro,Sekine, Mitsuo,Seio, Kohji. "DNA duplexes and triplex-forming oligodeoxynucleotides incorporating modified nucleosides forming stable and selective triplexes". supporting information; experimental part. p. 1007 - 1013. Retrieved 2012/04/10.
• 2、 Chen, Hauh-Jyun Candy,Row, Shin-Wei,Hong, Chia-Liang. "Detection and quantification of 5-chlorocytosine in DNA by stable isotope dilution and gas chromatography/negative ion chemical ionization/mass spectrometry". . p. 262 - 268. Retrieved 2007/10/03.