3'-azido-2',3'-dideoxy-5-bromouridine

Base Information

• Chemical Name: 3'-azido-2',3'-dideoxy-5-bromouridine
• CAS No.: 105784-82-5
• Molecular Formula: C₉H₁₀BrN₅O₄
• Molecular Weight: 332.113
• Mol file: 105784-82-5.mol

Synonyms:3'-Azido-2',3'-dideoxy-5-bromouridine

Chemical Property of 3'-azido-2',3'-dideoxy-5-bromouridine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 134.33000
• Density: g/cm³
• LogP: 0.12286

Purity/Quality:

99% ^*data from raw suppliers

3''-Azido-2'',3''-dideoxy-5-bromouridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3''-Azido-2'',3''-dideoxy-5-bromouridine can be used in biological study of virtual screening approach for thymidine monophosphate kinase inhibitors as antitubercular agents based on docking and pharmacophore models.

Technology Process of 3'-azido-2',3'-dideoxy-5-bromouridine

There total 3 articles about 3'-azido-2',3'-dideoxy-5-bromouridine 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: 76.0%

Navuridine (84472-85-5) → 3'-Azido-2',3'-dideoxy-5-bromouridine (105784-82-5)

Guidance literature:

With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2011.11.114

Reference yield:

3'-azido-5'-O-acetyl-2',3'-dideoxy-5-bromouridine (105784-85-8) → 3'-Azido-2',3'-dideoxy-5-bromouridine (105784-82-5)

Guidance literature:

With ammonia; In methanol; at 4 ℃; for 48h; Yield given;

DOI:10.1021/jm00385a033

Reference yield:

3'-azido-2',3'-dideoxy-5'-O-acetyluridine (84472-87-7) → 3'-Azido-2',3'-dideoxy-5-bromouridine (105784-82-5)

Guidance literature:

Multi-step reaction with 2 steps

1: glacial acetic acid, Br₂ / 4 °C

2: NH₃ / methanol / 48 h / 4 °C

With ammonia; bromine; acetic acid; In methanol;

DOI:10.1021/jm00385a033

upstream raw materials:

3'-azido-5'-O-acetyl-2',3'-dideoxy-5-bromouridine

Navuridine

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

Downstream raw materials:

2,5'-anhydro-3'-azido-2',3'-dideoxy-5-bromouridine

Refernces

• 1、 Lin,Chen,McLaren,Gao,Ghazzouli,Prusoff. "Synthesis and antiviral activity of various 3'-azido, 3'-amino, 2',3'-unsaturated, and 2',3'-dideoxy analogues of pyrimidine deoxyribonucleosides against retroviruses". . p. 440 - 444. Retrieved 2007/10/02.