(1S,2S)-4-(2,6-diamino-9H-purin-9-yl)cyclopentane-1,2-diol

Base Information

• Chemical Name: (1S,2S)-4-(2,6-diamino-9H-purin-9-yl)cyclopentane-1,2-diol
• CAS No.: 140438-63-7
• Molecular Formula: C₁₀H₁₄N₆O₂
• Molecular Weight: 250.26
• Mol file: 140438-63-7.mol

Synonyms:1,2-Cyclopentanediol,4-(2,6-diamino-9H-purin-9-yl)-, (1a,2b,4a)- (9CI); 1,2-Cyclopentanediol,4-(2,6-diamino-9H-purin-9-yl)-, (1a,2b,4a)-(?à)-

Chemical Property of (1S,2S)-4-(2,6-diamino-9H-purin-9-yl)cyclopentane-1,2-diol

Chemical Property:

• Vapor Pressure: 7.95E-18mmHg at 25°C
• Boiling Point: 650.8°Cat760mmHg
• Flash Point: 347.4°C
• Density: 2.06g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,2S)-4-(2,6-diamino-9H-purin-9-yl)cyclopentane-1,2-diol

There total 9 articles about (1S,2S)-4-(2,6-diamino-9H-purin-9-yl)cyclopentane-1,2-diol 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: 91.0%

(+/-)-(1α,2β,4β)-4-(2-amino-6-chloro-9H-purin-9-yl)-1,2-cyclopentanediol (140438-67-1) → (+/-)-(1α,2β,4β)-4-(2,6-diamino-9H-purin-9-yl)-1,2-cyclopentanediol (140438-63-7)

Guidance literature:

With ammonia; In methanol; at 100 ℃; for 48h;

DOI:10.1021/jm00090a007

Reference yield:

(+/-)-(1α,2β,4β)-4-amino-1,2-cyclopentanediol → (+/-)-(1α,2β,4β)-4-(2,6-diamino-9H-purin-9-yl)-1,2-cyclopentanediol (140438-63-7)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / butan-1-ol / 48 h / Heating

2: 75.5 percent / AcONa*3H₂O, glacial AcOH / H₂O / Ambient temperature

3: 65 percent / Zn, AcOH / ethanol; H₂O / 5 h / 80 - 85 °C

4: 2.) 0.5N HCl / 1.) 80 deg C, 20 h, 2.) H₂O, RT, 30 min

5: 91 percent / NH₃ / methanol / 48 h / 100 °C

With hydrogenchloride; ammonia; sodium acetate; acetic acid; triethylamine; zinc; In methanol; ethanol; water; butan-1-ol;

DOI:10.1021/jm00090a007

Reference yield:

4-benzamidocyclopentene (132065-12-4) → (+/-)-(1α,2β,4β)-4-(2,6-diamino-9H-purin-9-yl)-1,2-cyclopentanediol (140438-63-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / MCPBA / CHCl₃ / 1 h / Ambient temperature

2: 2percent aq.H₂SO₄ / 1 h / Ambient temperature

3: pyridine / Ambient temperature

4: 6N HCl / H₂O / 24 h / Heating

5: Et₃N / butan-1-ol / 48 h / Heating

6: 75.5 percent / AcONa*3H₂O, glacial AcOH / H₂O / Ambient temperature

7: 65 percent / Zn, AcOH / ethanol; H₂O / 5 h / 80 - 85 °C

8: 2.) 0.5N HCl / 1.) 80 deg C, 20 h, 2.) H₂O, RT, 30 min

9: 91 percent / NH₃ / methanol / 48 h / 100 °C

With pyridine; hydrogenchloride; sulfuric acid; ammonia; sodium acetate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In methanol; ethanol; chloroform; water; butan-1-ol;

DOI:10.1021/jm00090a007

upstream raw materials:

(+/-)-(1α,2β,4β)-4-(2-amino-6-chloro-9H-purin-9-yl)-1,2-cyclopentanediol

4-benzamidocyclopentene

(+/-)-(1α,2β,4α)-4-benzamidocyclopentane-1,2-diol

(+/-)-(1α,3α,4β)-N-<3,4-bis(acetyloxy)cyclopentenyl>benzamide