1,4-anhydro-2-(6-chloro-9H-purin-9-yl)-2-deoxypentitol

Base Information

• Chemical Name: 1,4-anhydro-2-(6-chloro-9H-purin-9-yl)-2-deoxypentitol
• CAS No.: 64332-71-4
• Molecular Formula: C₁₀H₁₁ClN₄O₃
• Molecular Weight: 270.675
• Mol file: 64332-71-4.mol

Synonyms:NSC253941

Chemical Property of 1,4-anhydro-2-(6-chloro-9H-purin-9-yl)-2-deoxypentitol

Chemical Property:

• Vapor Pressure: 9.72E-14mmHg at 25°C
• Boiling Point: 568°Cat760mmHg
• Flash Point: 297.3°C
• Density: 1.88g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,4-anhydro-2-(6-chloro-9H-purin-9-yl)-2-deoxypentitol

There total 8 articles about 1,4-anhydro-2-(6-chloro-9H-purin-9-yl)-2-deoxypentitol 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: 82.0%

4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol (259137-70-7) → 4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(hydroxymethyl)tetrahydrofuran-3(S)-ol (64332-71-4)

Guidance literature:

With ammonium fluoride; In methanol; Heating;

DOI:10.1080/07328319908044614

Reference yield:

1,4-anhydro-D-ribitol (491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9) → 4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(hydroxymethyl)tetrahydrofuran-3(S)-ol (64332-71-4)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 0 °C

2: 1.04 g / SOCl₂; pyridine / 20 °C

3: 78 percent / NaN₃ / dimethylformamide / 3 h / 80 °C

4: 91 percent / H₂ / Pd/C / ethanol / 6 h / 1292.87 Torr

5: 52 percent / pyridine / 1-methyl-pyrrolidin-2-one / 5 h / 140 °C

6: 90 percent / conc. HCl / 5 h / 20 °C

7: 82 percent / NH₄F / methanol / Heating

With pyridine; hydrogenchloride; ammonium fluoride; thionyl chloride; sodium azide; hydrogen; palladium on activated charcoal; In 1-methyl-pyrrolidin-2-one; methanol; ethanol; N,N-dimethyl-formamide; 1: Substitution / 2: Cyclization / 3: Ring cleavage / 4: Reduction / 5: Substitution / 6: Cyclization / 7: Substitution;

DOI:10.1080/07328319908044614

Reference yield:

2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol (215031-98-4) → 4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(hydroxymethyl)tetrahydrofuran-3(S)-ol (64332-71-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.04 g / SOCl₂; pyridine / 20 °C

2: 78 percent / NaN₃ / dimethylformamide / 3 h / 80 °C

3: 91 percent / H₂ / Pd/C / ethanol / 6 h / 1292.87 Torr

4: 52 percent / pyridine / 1-methyl-pyrrolidin-2-one / 5 h / 140 °C

5: 90 percent / conc. HCl / 5 h / 20 °C

6: 82 percent / NH₄F / methanol / Heating

With pyridine; hydrogenchloride; ammonium fluoride; thionyl chloride; sodium azide; hydrogen; palladium on activated charcoal; In 1-methyl-pyrrolidin-2-one; methanol; ethanol; N,N-dimethyl-formamide; 1: Cyclization / 2: Ring cleavage / 3: Reduction / 4: Substitution / 5: Cyclization / 6: Substitution;

DOI:10.1080/07328319908044614

upstream raw materials:

4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol

1,4-anhydro-D-ribitol

2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol

2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3R,4S)-disulfite

Refernces