2'-Deoxy-5-(2-cyanovinyl)uridine

Base Information

• Chemical Name: 2'-Deoxy-5-(2-cyanovinyl)uridine
• CAS No.: 80173-35-9
• Molecular Formula: C12H13 N3 O5
• Molecular Weight: 279.252
• Nikkaji Number: J1.622.295J,J2.654.814D
• ChEMBL ID: CHEMBL214700
• Mol file: 80173-35-9.mol

Synonyms:(E)-5-(2-cyanovinyl)-dUrd;2'-deoxy-5-(2-cyanovinyl)uridine;5-(2-cyanovinyl)-2'-deoxyuridine;5-CNV-DU

Chemical Property of 2'-Deoxy-5-(2-cyanovinyl)uridine

Chemical Property:

• PKA: 8.31±0.10(Predicted)
• PSA: 128.60000
• Density: 1.586±0.06 g/cm3(Predicted)
• LogP: -0.87362
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 279.08552052
• Heavy Atom Count: 20
• Complexity: 533

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)C=CC#N)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)/C=C/C#N)CO)O

Technology Process of 2'-Deoxy-5-(2-cyanovinyl)uridine

There total 2 articles about 2'-Deoxy-5-(2-cyanovinyl)uridine 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:

cyanomethylene triphenylphosphorane (16640-68-9) + 5-formyl-2'-deoxyuridine (4494-26-2) → (E)-5-(2-cyanovinyl)-2'-deoxyuridine (80173-35-9)

Guidance literature:

In methanol; at 60 ℃;

DOI:10.1021/acs.analchem.9b02499

Reference yield:

cyanomethylene triphenylphosphorane (16640-68-9) + 5-formyl-2'-deoxyuridine (4494-26-2) → (Z)-5-(2-cyanovinyl)-2'-deoxyuridine + (E)-5-(2-cyanovinyl)-2'-deoxyuridine (80173-35-9)

Guidance literature:

In methanol; water; Ambient temperature;

DOI:10.1248/cpb.42.2231

Reference yield: 58.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + (E)-5-(2-cyanovinyl)-2'-deoxyuridine (80173-35-9) → 5-(cyanovinyl)-2'-deoxy-5'-(dimethoxytrityl)uridine

Guidance literature:

With pyridine; dmap; triethylamine; at 20 ℃; for 16h;

DOI:10.1002/anie.200603161

upstream raw materials:

cyanomethylene triphenylphosphorane

5-formyl-2'-deoxyuridine

Refernces

• 1、 Ono,Okamoto,Inada,Nara,Matsuda. "Nucleosides and nucleotides. 131. Synthesis and properties of oligonucleotides containing 5-formyl-2'-deoxyuridine". . p. 2231 - 2237. Retrieved 2007/10/02.