(1S,2S,3R,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

Base Information

• Chemical Name: (1S,2S,3R,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
• CAS No.: 91382-84-2
• Molecular Formula: C11H15N5O3
• Molecular Weight: 265.272
• Mol file: 91382-84-2.mol

Synonyms:

Chemical Property of (1S,2S,3R,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

Chemical Property:

• Vapor Pressure: 5.19E-15mmHg at 25°C
• Boiling Point: 595.1°Cat760mmHg
• Flash Point: 313.7°C
• Density: 1.92g/cm³

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,2S,3R,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

There total 15 articles about (1S,2S,3R,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)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:

norborn-5-en-2-one (694-98-4) → (+/-)-4α-adenin-9-yl-2α,3β-dihydroxy-1α-cyclopentanemethanol (91382-84-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 71 percent / 35percent H₂O₂, conc. H₂SO₄ / diethyl ether / 2 h / Ambient temperature

2: KOH / dioxane / 1 h / Heating

3: dioxane / Heating

4: NEt₃ / acetone / 0.25 h / -5 °C

5: aq. NaN₃ / acetone / 0.5 h / -5 °C

6: toluene / 1 h / Heating

7: 40 percent / NaNO₂ / CH₂Cl₂ / Ambient temperature

8: 79 percent / m-CPBA / toluene / 0.5 h / Heating

9: 45 percent / Cs₂CO₃ / dimethylformamide / 48 h / 80 °C

10: 1) Na, 2) TFA, H₂ / 2) 10percent Pd-C / 1) MeOH, overnight, 2) MeOH, 50 psi, 6 h

With potassium hydroxide; sodium azide; sulfuric acid; hydrogen; dihydrogen peroxide; sodium; caesium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; sodium nitrite; palladium on activated charcoal; In 1,4-dioxane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1007/BF00807105

Reference yield:

(+-)-cis-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one (38110-76-8) → (+/-)-4α-adenin-9-yl-2α,3β-dihydroxy-1α-cyclopentanemethanol (91382-84-2)

Guidance literature:

Multi-step reaction with 9 steps

1: KOH / dioxane / 1 h / Heating

2: dioxane / Heating

3: NEt₃ / acetone / 0.25 h / -5 °C

4: aq. NaN₃ / acetone / 0.5 h / -5 °C

5: toluene / 1 h / Heating

6: 40 percent / NaNO₂ / CH₂Cl₂ / Ambient temperature

7: 79 percent / m-CPBA / toluene / 0.5 h / Heating

8: 45 percent / Cs₂CO₃ / dimethylformamide / 48 h / 80 °C

9: 1) Na, 2) TFA, H₂ / 2) 10percent Pd-C / 1) MeOH, overnight, 2) MeOH, 50 psi, 6 h

With potassium hydroxide; sodium azide; hydrogen; sodium; caesium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; sodium nitrite; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1007/BF00807105

Reference yield:

5-O-acetyl-1,2-anhydro-3-O-benzylcarba-α-DL-xylo-pentofuranose → (+/-)-4α-adenin-9-yl-2α,3β-dihydroxy-1α-cyclopentanemethanol (91382-84-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / Cs₂CO₃ / dimethylformamide / 48 h / 80 °C

2: 1) Na, 2) TFA, H₂ / 2) 10percent Pd-C / 1) MeOH, overnight, 2) MeOH, 50 psi, 6 h

With hydrogen; sodium; caesium carbonate; trifluoroacetic acid; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1007/BF00807105

upstream raw materials:

norborn-5-en-2-one

(+-)-cis-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

(+/-)-(1α,2β,3α,5α)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol

(+/-)-4α-acetamido-2α,3β-dihydroxy-1α-cyclopentanemethanol