N-[(4-Nitrophenyl)methyl]-9-pentofuranosyl-9H-purin-6-amine

Base Information

• Chemical Name: N-[(4-Nitrophenyl)methyl]-9-pentofuranosyl-9H-purin-6-amine
• CAS No.: 40297-54-9
• Molecular Formula: C17H18N6O6
• Molecular Weight: 402.367
• NSC Number: 127066
• DSSTox Substance ID: DTXSID80960734
• Mol file: 40297-54-9.mol

Synonyms:40297-54-9;NSC127066;SCHEMBL20626431;DTXSID80960734;NSC-127066;N-[(4-Nitrophenyl)methyl]-9-pentofuranosyl-9H-purin-6-amine

Chemical Property of N-[(4-Nitrophenyl)methyl]-9-pentofuranosyl-9H-purin-6-amine

Chemical Property:

• Vapor Pressure: 5.22E-25mmHg at 25°C
• Boiling Point: 771°Cat760mmHg
• Flash Point: 420.1°C
• PSA: 171.37000
• Density: 1.78g/cm³
• LogP: 0.55430
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 402.12878232
• Heavy Atom Count: 29
• Complexity: 573

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1CNC2=C3C(=NC=N2)N(C=N3)C4C(C(C(O4)CO)O)O)[N+](=O)[O-]

Technology Process of N-[(4-Nitrophenyl)methyl]-9-pentofuranosyl-9H-purin-6-amine

There total 7 articles about N-[(4-Nitrophenyl)methyl]-9-pentofuranosyl-9H-purin-6-amine 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: 88.0%

p-nitrobenzylamine (7409-30-5) + 6-Chloropurine riboside (2004-06-0) → N6-(p-Nirobenzyl)adenosine (40297-54-9)

Guidance literature:

With triethylamine; In neat (no solvent); at 210 ℃; for 0.0166667h; under 12929 Torr; Irradiation;

DOI:10.1016/j.bioorg.2019.103449

Reference yield:

4-nitrobenzylamine hydrochloride (18600-42-5) + 6-Chloropurine riboside (2004-06-0) → N6-(p-Nirobenzyl)adenosine (40297-54-9)

Guidance literature:

With triethylamine; In propan-1-ol; at 70 ℃; for 8h;

Reference yield:

2',3',5'-tri-O-acetylinosine (3181-38-2) → N6-(p-Nirobenzyl)adenosine (40297-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; trichlorophosphate / 0.12 h / 20 °C / Inert atmosphere

1.2: 0.22 h / Reflux

2.1: ammonia / methanol / 19 h / 0 - 20 °C

3.1: triethylamine / ethanol / 18 h / 60 °C

With dmap; ammonia; triethylamine; trichlorophosphate; In methanol; ethanol;

DOI:10.1021/acs.jmedchem.5b00802

upstream raw materials:

1-bromomethyl-4-nitro-benzene

adenosine

p-nitrobenzylamine

6-Chloropurine riboside

Downstream raw materials:

[125I]-N₆-(4-Aminobenzyl)adenosine

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(4-nitro-benzylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester

6-N-<4-(acetamido)benzyl>adenosine