6-Azacytidine

Base Information

• Chemical Name: 6-Azacytidine
• CAS No.: 3131-60-0
• Molecular Formula: C₈H₁₂N₄O₅
• Molecular Weight: 244.207
• European Community (EC) Number: 636-538-3
• UNII: YD42UEH51C
• DSSTox Substance ID: DTXSID4020117
• Nikkaji Number: J12.965H
• ChEMBL ID: CHEMBL1334069
• Mol file: 3131-60-0.mol

Synonyms:6-azacytidine

Chemical Property of 6-Azacytidine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.18E-13mmHg at 25°C
• Melting Point: 215 °C
• Refractive Index: 1.6590 (estimate)
• Boiling Point: 534.5 °C at 760 mmHg
• PKA: 13.44±0.70(Predicted)
• Flash Point: 277 °C
• PSA: 143.72000
• Density: 2.08 g/cm³
• LogP: -2.58680
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 244.08076950
• Heavy Atom Count: 17
• Complexity: 384

Purity/Quality:

97% ^*data from raw suppliers

6-Azacytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: C1=NN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O

Technology Process of 6-Azacytidine

There total 10 articles about 6-Azacytidine 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: 93.0%

N2-(2',3',5'-tri-O-acetyl)-β-D-ribofuranosyl-5-methylmercapto-1,2,4-triazin-3(2H)-one → 6-azacytidine (14528-15-5,3131-60-0)

Guidance literature:

With ammonium hydroxide; In ethanol; at 20 ℃;

DOI:10.1080/15257770.2015.1034363

Reference yield:

2',3',5'-tri-O-acetyl-6-azacytidine (20757-62-4) → 6-azacytidine (14528-15-5,3131-60-0)

Guidance literature:

With alkali medium;

DOI:10.1081/NCN-100002508

Reference yield:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(3-oxo-5-[1,2,4]triazol-1-yl-3H-[1,2,4]triazin-2-yl)-tetrahydro-furan-3-yl ester (257297-86-2) → 6-azacytidine (14528-15-5,3131-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 226 mg / NH₄Cl; DBU / pyridine / 24 h / 20 °C

2: NH₃ / methanol / 24 h / 20 °C

With ammonia; ammonium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; methanol;

DOI:10.1021/ja001918t

upstream raw materials:

2',3',5'-tri-O-acetyl-6-azacytidine

1,2,3,5-tetra-O-acetyl-D-ribofuranose

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(3-oxo-5-[1,2,4]triazol-1-yl-3H-[1,2,4]triazin-2-yl)-tetrahydro-furan-3-yl ester

6-Azauridine

Refernces

• 1、 Alexeeva, Inna,Nosach, Lydia,Palchykovska, Larisa,Usenko, Lyubov,Povnitsa, Olga. "Synthesis and Comparative Study of Anti-Adenoviral Activity of 6-Azacytidine and Its Analogues". . p. 565 - 578. Retrieved 2015/10/12.
• 2、 Oyelere,Strobel. "Biochemical detection of cytidine protonation within RNA". . p. 10259 - 10267. Retrieved 2007/10/03.