9-[(1R,4S)-4-methoxy-1-cyclopent-2-enyl]purin-6-amine

Base Information

• Chemical Name: 9-[(1R,4S)-4-methoxy-1-cyclopent-2-enyl]purin-6-amine
• CAS No.: 194606-97-8
• Molecular Formula: C11H13N5O
• Molecular Weight: 231.2538
• Mol file: 194606-97-8.mol

Synonyms:

Chemical Property of 9-[(1R,4S)-4-methoxy-1-cyclopent-2-enyl]purin-6-amine

Chemical Property:

• Vapor Pressure: 6.5E-09mmHg at 25°C
• Boiling Point: 467.5°Cat760mmHg
• Flash Point: 236.5°C
• Density: 1.52g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 9-[(1R,4S)-4-methoxy-1-cyclopent-2-enyl]purin-6-amine

There total 7 articles about 9-[(1R,4S)-4-methoxy-1-cyclopent-2-enyl]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:

N-[9-((1R,4S)-4-Methoxy-cyclopent-2-enyl)-9H-purin-6-yl]-benzamide (194606-93-4) → (+)-9-(cis-4-methoxycyclopenten-2-yl)-adenine (194606-97-8)

Guidance literature:

With ammonium hydroxide; In water; at 110 ℃; for 48h;

DOI:10.1021/jo970515h

Reference yield:

(1S,4R)-4-hydroxy-2-cyclopentenyl acetate (60176-77-4) → (+)-9-(cis-4-methoxycyclopenten-2-yl)-adenine (194606-97-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 44.0 g / imidazole / dimethylformamide / 6 h / Ambient temperature

2: 7.7 g / K₂CO₃ / methanol / 0.5 h / Ambient temperature

3: 62 percent / KOH / dimethylsulfoxide / 4 h / Ambient temperature

4: 59 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

5: 58 percent / DMAP / pyridine; CH₂Cl₂ / Ambient temperature

6: 1.) NaH, 2.) Pd(PPh₃)4 / 1.) DMSO, rt, 30 min, 2.) DMSO, THF, 55 deg C, 2 d

7: 0.69 g / NH₄OH / H₂O / 48 h / 110 °C

With 1H-imidazole; dmap; potassium hydroxide; ammonium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo970515h

Reference yield:

(1S,4R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enol (104069-09-2) → (+)-9-(cis-4-methoxycyclopenten-2-yl)-adenine (194606-97-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / KOH / dimethylsulfoxide / 4 h / Ambient temperature

2: 59 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

3: 58 percent / DMAP / pyridine; CH₂Cl₂ / Ambient temperature

4: 1.) NaH, 2.) Pd(PPh₃)4 / 1.) DMSO, rt, 30 min, 2.) DMSO, THF, 55 deg C, 2 d

5: 0.69 g / NH₄OH / H₂O / 48 h / 110 °C

With dmap; potassium hydroxide; ammonium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; pyridine; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1021/jo970515h

upstream raw materials:

N-[9-((1R,4S)-4-Methoxy-cyclopent-2-enyl)-9H-purin-6-yl]-benzamide

(1S,4R)-4-hydroxy-2-cyclopentenyl acetate

(1S,4R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enol

(1R,3S)-(-)-1-acetoxycyclopentan-3-ol