2-Aminoadenosine

Base Information

• Chemical Name: 2-Aminoadenosine
• CAS No.: 2096-10-8
• Molecular Formula: C10H14N6O4
• Molecular Weight: 282.259
• Hs Code.: 29389090
• UNII: CCF94TM2UR
• DSSTox Substance ID: DTXSID001346570
• Nikkaji Number: J616.886H
• Wikidata: Q27105391
• Metabolomics Workbench ID: 67867
• ChEMBL ID: CHEMBL255442
• Mol file: 2096-10-8.mol

Synonyms:2,6-diaminopurine ribonucleoside;2,6-diaminopurine riboside;2-aminoadenosine

Chemical Property of 2-Aminoadenosine

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 241-243°C (dec.)
• Boiling Point: 798.5 °C at 760 mmHg
• PKA: 13.10±0.70(Predicted)
• Flash Point: 436.7 °C
• PSA: 165.56000
• Density: 2.25 g/cm³
• LogP: -1.23540
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Aqueous Acid (Slightly, Heated, Sonicated), DMSO (Slightly, Sonicated), Ethanol
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 282.10765295
• Heavy Atom Count: 20
• Complexity: 363

Purity/Quality:

99% ^*data from raw suppliers

2-Aminoadenosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)CO)O)O)N)N
• Isomeric SMILES: C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N)N
• Description: 2-Aminoadenosine is a known analogue of adenosine that engages in three hydrogen bonds of the W-C type, adding considerable stability to the double helix.
• Uses: 2-Aminoadenosine is a nucleoside analog as inhibitor or substrate of adenosine kinase from M. tuberculosis. It is also used to synthesize 2′-O-methyl and 3′-O-methyl Guanosine.

Technology Process of 2-Aminoadenosine

There total 2 articles about 2-Aminoadenosine 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: 21.0%

1-phenylcyanamide (622-34-4) + 5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile (23192-64-5) → 2-phenylaminoadenosine (53296-10-9) + adenosine-2-amine (2096-10-8)

Guidance literature:

With ammonia; In methanol; at 150 ℃; for 5h;

DOI:10.1248/cpb.29.1870

Reference yield:

methanol (67-56-1) + 2-amino-6-chloro-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine (3387-63-1) → 2-Amino-6-chloropurine riboside (2004-07-1) + 6-O-methylguanosine (7803-88-5) + adenosine-2-amine (2096-10-8)

Guidance literature:

With ammonia; at 50 ℃; for 16h;

DOI:10.1021/jo061885l

Reference yield: 82.0%

methylene-bis(diisopropylsilyl chloride) (473278-50-1) + adenosine-2-amine (2096-10-8) → (2R,3R,3aS,9aR)-2-(2,6-Diamino-purin-9-yl)-5,5,7,7-tetraisopropyl-hexahydro-1,4,8-trioxa-5,7-disila-cyclopentacycloocten-3-ol

Guidance literature:

DOI:10.1021/jo025970e

upstream raw materials:

1-phenylcyanamide

5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile

methanol

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

Downstream raw materials:

2-fluoroadenosine

isoguanosine

2,6-diamino-9-(3-O-methyl-β-D-ribofuranosyl)purine

2-amino-2'-O-methyladenosine

Refernces

• 1、 Omura,Marumoto,Furukawa. "Synthesis of 2-phenylaminoadenosine from imidazole nucleosides". . p. 1870 - 1875. Retrieved 2007/10/02.