2-Bromoadenosine

Base Information

• Chemical Name: 2-Bromoadenosine
• CAS No.: 146-76-9
• Molecular Formula: C10H12BrN5O4
• Molecular Weight: 346.14
• DSSTox Substance ID: DTXSID30445546
• Wikidata: Q82264000
• Mol file: 146-76-9.mol

Synonyms:2-Bromoadenosine;146-76-9;Adenosine, 2-bromo-;(2R,3R,4S,5R)-2-(6-AMINO-2-BROMOPURIN-9-YL)-5-(HYDROXYMETHYL)OXOLANE-3,4-DIOL;(2R,3R,4S,5R)-2-(6-Amino-2-bromo-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol;SCHEMBL7038406;DTXSID30445546;(2R,3R,4S,5R)-2-(6-amino-2-bromo-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Chemical Property of 2-Bromoadenosine

Chemical Property:

• PSA: 139.54000
• LogP: -0.63630
• XLogP3: 0
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 345.00727
• Heavy Atom Count: 20
• Complexity: 367

Purity/Quality:

98%min ^*data from raw suppliers

2-Bromoadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)CO)O)O)Br)N
• Isomeric SMILES: C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)Br)N

Technology Process of 2-Bromoadenosine

There total 9 articles about 2-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: 82.0%

2-Bromo-6-chloro-9β-(2',3',5'-tri-O-acetyl)-D-ribofuranosylpurine (40896-58-0) → 2-Bromo-adenosine (146-76-9)

Guidance literature:

With ammonia; In ethanol; at 20 ℃; for 1h;

DOI:10.1021/jm990156d

Reference yield: 69.0%

2-bromo-2',3′,5′-tri-O-(t-butyldimethylsilyl)adenosine (129399-00-4) → 2-Bromo-adenosine (146-76-9)

Guidance literature:

With potassium fluoride; In methanol; at 80 ℃; for 24h;

DOI:10.3390/molecules201018437

Reference yield:

2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (16321-99-6) → 2-Bromo-adenosine (146-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / t-butyl nitrite, CHBr₃ / 4.5 h / 20 - 85 °C

2: 80 percent / NH₃ / methanol

With tert.-butylnitrite; Bromoform; ammonia; In methanol;

DOI:10.1002/(SICI)1099-1344(199608)38:8<743::AID-JLCR884>3.0.CO;2-F

upstream raw materials:

2-Bromo-6-chloro-9β-(2',3',5'-tri-O-acetyl)-D-ribofuranosylpurine

methanol

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

G

Downstream raw materials:

2-(n-butoxy)adenosine

2-methyladenosine

Refernces

• 1、 Satishkumar, Sakilam,Vuram, Prasanna K.,Relangi, Siva Subrahmanyam,Gurram, Venkateshwarlu,Zhou, Hong,Kreitman, Robert J.,Montemayor, Michelle M. Martínez,Yang, Lijia,Kaliyaperumal, Muralidharan,Sharma, Somesh,Pottabathini, Narender,Lakshman, Mahesh K.. "Cladribine analogues via O6-(benzotriazolyl) derivatives of guanine nucleosides". . p. 18437 - 18463. Retrieved 2015.
• 2、 Halbfinger, Efrat,Major, Dan T.,Ritzmann, Marco,Ubl, Joachim,Reiser, Georg,Boyer, Jose L.,Harden, Kendall T.,Fischer, Bilha. "Molecular recognition of modified adenine nucleotides by the P2Y1-receptor. 1. A synthetic, biochemical, and NMR approach". . p. 5325 - 5337. Retrieved 2007/10/03.