3'-Amino-2',3'-dideoxycytidine

Base Information

• Chemical Name: 3'-Amino-2',3'-dideoxycytidine
• CAS No.: 84472-90-2
• Molecular Formula: C9H14N4O3
• Molecular Weight: 226.235
• Nikkaji Number: J500.513B
• ChEMBL ID: CHEMBL1791179
• Mol file: 84472-90-2.mol

Synonyms:3'-amino-2',3'-dideoxycytidine

Chemical Property of 3'-Amino-2',3'-dideoxycytidine

Chemical Property:

• Boiling Point: 450.2 °C at 760 mmHg
• Flash Point: 226 °C
• PSA: 116.39000
• Density: 1.73 g/cm³
• LogP: -0.28590
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 226.10659032
• Heavy Atom Count: 16
• Complexity: 355

Purity/Quality:

99% ^*data from raw suppliers

3''-Amino-2'',3''-dideoxycytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=CC(=NC2=O)N)CO)N
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)N)CO)N
• Uses: 3''-Amino-2'',3''-dideoxycytidine CAn be used to recognized Cytidine Deaminase. In doing so it can be effective in the treatment of leukemia.

Technology Process of 3'-Amino-2',3'-dideoxycytidine

There total 14 articles about 3'-Amino-2',3'-dideoxycytidine 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: 68.0%

3'-azido-2',3'-dideoxycytidine (84472-89-9) → 3'-amino-2',3'-dideoxycytidine (84472-90-2)

Guidance literature:

With pyridine; ammonium hydroxide; triphenylphosphine;

DOI:10.1080/15257779408013281

Reference yield: 65.0%

3'-azido-2',3'-dideoxycytidine hydrochloride (85236-96-0) → 3'-amino-2',3'-dideoxycytidine (84472-90-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 24 ℃; for 1.5h;

DOI:10.1021/jm00360a019

Reference yield:

3'-azido-2',3'-dideoxy-5'-O-acetyluridine (84472-87-7) → 3'-amino-2',3'-dideoxycytidine (84472-90-2)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / CHCl₃; dimethylformamide / 6 h / Heating

2: 31 percent / NH₃ / methanol / 144 h / Ambient temperature

3: 65 percent / H₂ / 10percent Pd/C / methanol / 2 h / 2585.7 Torr

With thionyl chloride; ammonia; hydrogen; palladium on activated charcoal; In methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm00358a016

upstream raw materials:

3'-azido-2',3'-dideoxycytidine

3'-azido-2',3'-dideoxycytidine hydrochloride

3'-azido-2',3'-dideoxy-5'-O-tritylcytidine

Navuridine

Downstream raw materials:

3'-NH-trityl-2',3'-dideoxycytidine

N₄-benzoyl-3'-aminotrityl-2',3'-dideoxycytidine

Refernces

• 1、 Zaitseva,Kvasyuk,Vaaks,Barai,Bokut,Zinchenko,Mikhailopulo. "Chemical-enzymatic synthesis of 3'-amino-2',3'-dideoxy-β-D- ribofuranosides of natural heterocyclic bases and their 5'-monophosphates". . p. 819 - 834. Retrieved 2007/10/02.
• 2、 Lin, Tai-Shun,Gao, You-Song,Mancini, William R.. "Synthesis and Biological Activity of Various 3'-Azido and 3'-Amino Analogues of 5-Substituted Pyrimidine Deoxyribonucleosides". . p. 1691 - 1696. Retrieved 2007/10/02.