2-Bromo-2'-deoxyadenosine

Base Information

• Chemical Name: 2-Bromo-2'-deoxyadenosine
• CAS No.: 89178-21-2
• Molecular Formula: C10H12 Br N5 O3
• Molecular Weight: 330.141
• Nikkaji Number: J22.928H
• ChEMBL ID: CHEMBL3143081
• Mol file: 89178-21-2.mol

Synonyms:2'-deoxy-2-bromoadenosine;2-bromo-2'-deoxyadenosine;BrdAdo

Chemical Property of 2-Bromo-2'-deoxyadenosine

Chemical Property:

• Vapor Pressure: 1.38E-21mmHg at 25°C
• Boiling Point: 717.2°C at 760 mmHg
• Flash Point: 387.5°C
• PSA: 119.31000
• Density: 2.3g/cm³
• LogP: 0.39290
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 329.01235
• Heavy Atom Count: 19
• Complexity: 338

Purity/Quality:

97% ^*data from raw suppliers

2-BROMO-2'-DEOXYADENOSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=NC3=C(N=C(N=C32)Br)N)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=C(N=C32)Br)N)CO)O

Technology Process of 2-Bromo-2'-deoxyadenosine

There total 9 articles about 2-Bromo-2'-deoxyadenosine 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%

2,6-dibromo-9-(2-deoxy-3,5-di-p-toluoyl-β-D-ribofuranosyl)purine (110096-57-6) → 2-bromo-2′-deoxyadenosine (89178-21-2)

Guidance literature:

With ammonia; In methanol; at 60 ℃; for 32h;

DOI:10.1021/jo00229a037

Reference yield: 66.0%

2-bromo-3′,5′-di-O-(t-butyldimethylsilyl)-2′-deoxyadenosine → 2-bromo-2′-deoxyadenosine (89178-21-2)

Guidance literature:

With potassium fluoride; In methanol; at 80 ℃; for 28h;

DOI:10.3390/molecules201018437

Reference yield:

2,6-dibromopurine (1196-41-4) → 2-bromo-2′-deoxyadenosine (89178-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₃ / ethanol / 100 °C

2: nucleoside deoxyribosyl transferase

With ammonia; In ethanol;

DOI:10.1021/jm00372a017

upstream raw materials:

2,6-dibromo-9-(2-deoxy-3,5-di-p-toluoyl-β-D-ribofuranosyl)purine

2-bromo-9H-purin-6-amine

thymidine

purine-2,6(1H,3H)-dithione

Downstream raw materials:

2-bromo-9-<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl>-6-<<(dimethylamino)methylidene>amino>-9H-purine 3'-triethylammonium phosphonate

2-bromo-9-<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl>-6-<<(dimethylamino)methylidene>amino>-9H-purine

2'-deoxyspongosine

2'-deoxy-D-adenosine

Refernces

• 1、 -. "Process for the production of 2-halo-6-aminopurine derivatives". . . Retrieved 2008/06/13.
• 2、 Huang,Avery,Blakley,Secrist III,Montgomery. "Improved synthesis and antitumor activity of 2-bromo-2'- deoxyadenosine". . p. 800 - 802. Retrieved 2007/10/02.