3'-azidothymidine-5'-(p-bromophenyl)methoxyalaninyl phosphate

Base Information

• Chemical Name: 3'-azidothymidine-5'-(p-bromophenyl)methoxyalaninyl phosphate
• CAS No.: 220693-38-9
• Molecular Formula: C₂₀H₂₄BrN₆O₈P
• Molecular Weight: 587.324
• Mol file: 220693-38-9.mol

Synonyms:3'-azidothymidine-5'-(p-bromophenyl)methoxyalaninyl phosphate

Chemical Property of 3'-azidothymidine-5'-(p-bromophenyl)methoxyalaninyl phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-azidothymidine-5'-(p-bromophenyl)methoxyalaninyl phosphate

There total 4 articles about 3'-azidothymidine-5'-(p-bromophenyl)methoxyalaninyl phosphate 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: 95.0%

p-bromophenyl methoxyalaninyl phosphorochloridate + 3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2) → 3'-azidothymidine-5'-(p-bromophenyl)methoxyalaninyl phosphate (220693-38-9)

Guidance literature:

With 1-methyl-1H-imidazole; In tetrahydrofuran;

Reference yield: 83.0%

3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2) + 4-bromophenyl methoxy-alanyl phosphorochloridate (217090-42-1) → 3'-azidothymidine-5'-(p-bromophenyl)methoxyalaninyl phosphate (220693-38-9)

Guidance literature:

With 1-methyl-1H-imidazole; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmc.2005.02.031

Reference yield:

4-bromo-phenol (106-41-2) → 3'-azidothymidine-5'-(p-bromophenyl)methoxyalaninyl phosphate (220693-38-9)

Guidance literature:

Multi-step reaction with 3 steps

1: phosphorus oxychloride; triethylamine / diethyl ether / 0 - 20 °C

2: triethylamine / CH₂Cl₂ / -70 - 20 °C

3: 83 percent / N-methylimidazole / tetrahydrofuran / 20 °C

With 1-methyl-1H-imidazole; triethylamine; trichlorophosphate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/j.bmc.2005.02.031

upstream raw materials:

3'-azido-2',3'-deoxythymidine

4-bromophenyl methoxy-alanyl phosphorochloridate

4-bromo-phenol

p-bromophenyl phosphorodichloridate

Downstream raw materials:

4-bromo-phenol

2(S)-(3-deoxy-3-azidothymidyl(hydroxy)phosphorylamino)propionic acid methyl ester

5-bromo-6-methoxy-5,6-dihydro-3'-azidothymidine-5'-(p-bromophenyl) methoxyalaninyl phosphate

Refernces

• 1、 Benyumov, Alexey O.,Venkatachalam, Taracad K.,Grigoriants, Olga O.,Vassilev, Alexei O.,Tibbles, Heather E.,Downs, Suzanne,Dumez, Darin,Uckun, Fatih M.. "Anti-proliferative and anti-leukemic activity of DDE46 (compound WHI-07), a novel bromomethoxylated arylphosphate derivative of zidovudine, and related compounds: Studies using human acute lymphoblastic leukemia cells and the zebrafish model". . p. 114 - 122. Retrieved 2007/10/03.