5-Chlorouridine

Base Information

• Chemical Name: 5-Chlorouridine
• CAS No.: 2880-89-9
• Molecular Formula: C9H11ClN2O6
• Molecular Weight: 278.65
• Hs Code.: 2934999090
• Nikkaji Number: J331.852D
• ChEMBL ID: CHEMBL2206659
• Mol file: 2880-89-9.mol

Synonyms:5-chlorouridine

Chemical Property of 5-Chlorouridine

Chemical Property:

• Melting Point: 215-217°C
• Refractive Index: 1.677
• PKA: 7.73±0.10(Predicted)
• PSA: 124.78000
• Density: 1.804 g/cm³
• LogP: -2.19850
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Methanol, Water (Slightly, Sonicated)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 278.0305638
• Heavy Atom Count: 18
• Complexity: 414

Purity/Quality:

97% ^*data from raw suppliers

5-Chlorouridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)Cl
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)Cl
• Uses: 5-Chlorouridine is used in method of determining the activity of enzymes converting Cytosine derivatives to Uracil derivatives in cells, tissues and organisms.

Technology Process of 5-Chlorouridine

There total 10 articles about 5-Chlorouridine 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: 94.0%

uridine (58-96-8) → 5-chlorouridine (2880-89-9)

Guidance literature:

With 1-(2-methoxyethyl)-3-methylimidazolium trifluoroacetate; N-chloro-succinimide; at 50 ℃; for 0.75h;

DOI:10.1055/s-0029-1217042

Reference yield: 90.4%

uridine (58-96-8) → 5-chlorouridine (2880-89-9)

Guidance literature:

With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid; In N,N-dimethyl acetamide; for 2h; Ambient temperature;

DOI:10.1021/jo00326a053

Reference yield: 88.0%

2',3',5'-tri-O-acetyl-5-chlorouridine (3370-68-1,3266-87-3) → 5-chlorouridine (2880-89-9)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo00303a033

upstream raw materials:

uridine

2',3',5'-tri-O-acetyl-5-chlorouridine

Tri-O-acetyluridine

1,2,3,5-tetraacetylribose

Downstream raw materials:

5'-deoxy-5'-iodo-2',3'-O-isopropylidene-5-chlorouridine

2',3'-O-isopropylidene-5-chlorouridine

2'-O-trityl-5-chlorouridine

3',5'-di-O-trityl-5-chlorouridine

Refernces

• 1、 Alexeev, Cyril S.,Drenichev, Mikhail S.,Dorinova, Evgeniya O.,Esipov, Roman S.,Kulikova, Irina V.,Mikhailov, Sergey N.. "Use of nucleoside phosphorylases for the preparation of 5-modified pyrimidine ribonucleosides". . . Retrieved 2019/11/13.
• 2、 Chatelain, Grégory,Debing, Yannick,De Burghgraeve, Tine,Zmurko, Joanna,Saudi, Milind,Rozenski, Jef,Neyts, Johan,Van Aerschot, Arthur. "In search of flavivirus inhibitors: Evaluation of different tritylated nucleoside analogues". . p. 249 - 255. Retrieved 2013/10/01.