9-[3-Deoxy-3-(hydroxymethyl)pentofuranosyl]-9h-purin-6-amine

Base Information

• Chemical Name: 9-[3-Deoxy-3-(hydroxymethyl)pentofuranosyl]-9h-purin-6-amine
• CAS No.: 26289-43-0
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 281.271
• NSC Number: 127969
• DSSTox Substance ID: DTXSID80299076
• Mol file: 26289-43-0.mol

Synonyms:26289-43-0;NSC127969;9-[3-deoxy-3-(hydroxymethyl)pentofuranosyl]-9h-purin-6-amine;DTXSID80299076;NSC-127969;2-(6-amino-9H-purin-9-yl)-4,5-bis(hydroxymethyl)tetrahydrofuran-3-ol

Chemical Property of 9-[3-Deoxy-3-(hydroxymethyl)pentofuranosyl]-9h-purin-6-amine

Chemical Property:

• Vapor Pressure: 1.43E-19mmHg at 25°C
• Boiling Point: 682.6°Cat760mmHg
• Flash Point: 366.7°C
• Density: 1.94g/cm³
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 281.11240398
• Heavy Atom Count: 20
• Complexity: 349

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)CO)O)N

Technology Process of 9-[3-Deoxy-3-(hydroxymethyl)pentofuranosyl]-9h-purin-6-amine

There total 12 articles about 9-[3-Deoxy-3-(hydroxymethyl)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: 99.0%

6-chloro-9-<5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-2-O-acetyl-β-D-ribofuranosyl>-9H-purine (130469-50-0) → 6-amino-9-<3-deoxy-3-(hydroxymethyl)-β-D-ribofuranosyl>-9H-purine (26289-43-0)

Guidance literature:

With ammonia; at 100 ℃; for 48h;

DOI:10.1021/jm00105a054

Reference yield:

6-chloro-9-trimethylsilylpurine (32865-86-4) → 6-amino-9-<3-deoxy-3-(hydroxymethyl)-β-D-ribofuranosyl>-9H-purine (26289-43-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / trimethylsilyl triflate / acetonitrile / 0.25 h / Ambient temperature

2: 99 percent / methanolic ammonia / 48 h / 100 °C

With trimethylsilyl trifluoromethanesulfonate; ammonia; In acetonitrile;

DOI:10.1021/jm00105a054

Reference yield:

5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-1,2-di-O-acetyl-β-D-ribofuranose (130469-49-7) → 6-amino-9-<3-deoxy-3-(hydroxymethyl)-β-D-ribofuranosyl>-9H-purine (26289-43-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / trimethylsilyl triflate / acetonitrile / 0.25 h / Ambient temperature

2: 99 percent / methanolic ammonia / 48 h / 100 °C

With trimethylsilyl trifluoromethanesulfonate; ammonia; In acetonitrile;

DOI:10.1021/jm00105a054

upstream raw materials:

9-<3'-deoxy-3'-<(benzyloxy)methyl>-2,5-di-O-benzoyl-β-D-ribofuranosyl>-6-chloropurine

6-chloro-9-<5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-2-O-acetyl-β-D-ribofuranosyl>-9H-purine

6-chloro-9-trimethylsilylpurine

5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-1,2-di-O-acetyl-β-D-ribofuranose

Downstream raw materials:

Thiocarbonic acid O-[(2R,3R,4R,5S)-2-(6-amino-purin-9-yl)-4,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester O-phenyl ester