(E)-5-(2-Chlorovinyl)-6-aza-2'-deoxyuridine

Base Information

• Chemical Name: (E)-5-(2-Chlorovinyl)-6-aza-2'-deoxyuridine
• CAS No.: 100348-18-3
• Molecular Formula: C₁₀H₁₂ClN₃O₅
• Molecular Weight: 289.675
• Mol file: 100348-18-3.mol

Synonyms:(E)-5-(2-Chlorovinyl)-6-aza-2'-deoxyuridine;100348-18-3;(E)-5-(2-Chlorovinyl0-6-aza-2'-deoxyuridine;6-[(E)-2-chlorovinyl]-2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,2,4-triazine-3,5-dione

Chemical Property of (E)-5-(2-Chlorovinyl)-6-aza-2'-deoxyuridine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.79g/cm³
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 289.0465482
• Heavy Atom Count: 19
• Complexity: 452

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(=O)NC(=O)C(=N2)C=CCl)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C(=O)NC(=O)C(=N2)/C=C/Cl)CO)O

Technology Process of (E)-5-(2-Chlorovinyl)-6-aza-2'-deoxyuridine

There total 3 articles about (E)-5-(2-Chlorovinyl)-6-aza-2'-deoxyuridine 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: 51.0%

(E)-5-(2-chlorovinyl)-1-(2'-deoxy-3'-5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-azauracil (97776-77-7) → (E)-5-(2-chlorovinyl)-6-aza-2'-deoxyuridine (100348-18-3)

Guidance literature:

With potassium carbonate; In methanol; for 16h; Ambient temperature;

DOI:10.1021/jm00155a035

Reference yield:

5-hydroxymethyl-(3,5-di-O-p-toluoyl)-6-aza-2-deoxyuridine (20258-32-6) → (E)-5-(2-chlorovinyl)-6-aza-2'-deoxyuridine (100348-18-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / diphenyl diselenide, 70percent aq. tert-butyl hydroperoxide / benzene / 4.5 h / Heating

2: 1.) n-butyllithium / 1.) THF, -70 deg C, 20 min, 2.) THF, -70 deg C, 10 min

3: 51 percent / potassium carbonate / methanol / 16 h / Ambient temperature

With tert.-butylhydroperoxide; n-butyllithium; diphenyl diselenide; potassium carbonate; In methanol; benzene;

DOI:10.1021/jm00155a035

Reference yield:

5-formyl-1-(2'-deoxy-3'-5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-azauracil (97776-66-4) → (E)-5-(2-chlorovinyl)-6-aza-2'-deoxyuridine (100348-18-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-butyllithium / 1.) THF, -70 deg C, 20 min, 2.) THF, -70 deg C, 10 min

2: 51 percent / potassium carbonate / methanol / 16 h / Ambient temperature

With n-butyllithium; potassium carbonate; In methanol;

DOI:10.1021/jm00155a035

upstream raw materials:

(E)-5-(2-chlorovinyl)-1-(2'-deoxy-3'-5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-azauracil

5-hydroxymethyl-(3,5-di-O-p-toluoyl)-6-aza-2-deoxyuridine

5-formyl-1-(2'-deoxy-3'-5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-azauracil