2-Amino-8-bromoadenosine

Base Information

• Chemical Name: 2-Amino-8-bromoadenosine
• CAS No.: 81102-44-5
• Molecular Formula: C₁₀H₁₃BrN₆O₄
• Molecular Weight: 361.155
• DSSTox Substance ID: DTXSID90559951
• Nikkaji Number: J2.591.255A
• Wikidata: Q82442849
• Mol file: 81102-44-5.mol

Synonyms:2-amino-8-bromoadenosine;8-Br-2AA;8-bromo-2-aminoadenosine

Chemical Property of 2-Amino-8-bromoadenosine

Chemical Property:

• PSA: 166.29000
• LogP: -1.12400
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 360.01817
• Heavy Atom Count: 21
• Complexity: 395

Purity/Quality:

97% ^*data from raw suppliers

(2R,3R,4S,5R)-2-(2,6-Diamino-8-bromo-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(O1)N2C3=NC(=NC(=C3N=C2Br)N)N)O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@H]([C@@H](O1)N2C3=NC(=NC(=C3N=C2Br)N)N)O)O)O

Technology Process of 2-Amino-8-bromoadenosine

There total 7 articles about 2-Amino-8-bromoadenosine 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: 98.0%

adenosine-2-amine (2096-10-8) → 9-(β-D-ribofuranosyl)-2,6-diamino-8-bromopurine (81102-44-5)

Guidance literature:

With bromine; In water; at 20 ℃;

DOI:10.1021/acs.orglett.9b03801

Reference yield:

2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (16321-99-6) → 9-(β-D-ribofuranosyl)-2,6-diamino-8-bromopurine (81102-44-5)

Guidance literature:

Multi-step reaction with 4 steps

1: NaN₃ / acetonitrile

2: H₂ / Pd-C

3: NH₃ / methanol

4: 71 percent / N-bromosuccinimide / H₂O / 0.08 h / Ambient temperature

With N-Bromosuccinimide; sodium azide; ammonia; hydrogen; palladium on activated charcoal; In methanol; water; acetonitrile;

DOI:10.1002/jhet.5570320331

Reference yield:

2-amino-6-azido-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-purine (79999-42-1) → 9-(β-D-ribofuranosyl)-2,6-diamino-8-bromopurine (81102-44-5)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd-C

2: NH₃ / methanol

3: 71 percent / N-bromosuccinimide / H₂O / 0.08 h / Ambient temperature

With N-Bromosuccinimide; ammonia; hydrogen; palladium on activated charcoal; In methanol; water;

DOI:10.1002/jhet.5570320331

upstream raw materials:

adenosine-2-amine

9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2,6-diaminopurine

2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

2-amino-6-azido-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-purine

Downstream raw materials:

2-amino-2'-deoxyadenosine

2,6-diamino-8-bromo-9-(2'-O-tosyl-β-D-ribufuranosyl)-purine

Refernces

• 1、 Ozola,Persson,Gronowitz,Hornfeldt. "On the syntheses of 8-heteroaryl-substituted 9-(β-D-ribofuranosyl)-2,6-diaminopurines through Pd-catalyzed coupling in the presence of cupric oxide". . p. 863 - 866. Retrieved 2007/10/02.