6-chloro-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine

Base Information

• Chemical Name: 6-chloro-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine
• CAS No.: 109304-00-9
• Molecular Formula: C₁₉H₁₆ClFN₄O₅
• Molecular Weight: 434.811
• Mol file: 109304-00-9.mol

Synonyms:6-chloro-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine

Chemical Property of 6-chloro-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-chloro-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine

There total 3 articles about 6-chloro-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine 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:

1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (56632-81-6) + 6-chloropurine (87-42-3) → 6-chloro-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine (109304-00-9)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; for 1h; Yield given; Ambient temperature;

DOI:10.1021/jm00165a015

Reference yield:

1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose (84025-00-3) → 6-chloro-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine (109304-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 30percent HBr / CH₂Cl₂; acetic acid / 1 h

2: 4A molecular sieves / CH₂Cl₂ / 15 h / Heating

With 4 A molecular sieve; hydrogen bromide; In dichloromethane; acetic acid;

DOI:10.1021/jm00165a015

Reference yield:

1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (56632-81-6) + 6-chloropurine (87-42-3) → Benzoic acid (2R,3R,4S,5R)-3-acetoxy-5-(6-chloro-purin-7-yl)-4-fluoro-tetrahydro-furan-2-ylmethyl ester (125542-14-5) + Benzoic acid (2R,3R,4S,5S)-3-acetoxy-5-(6-chloro-purin-7-yl)-4-fluoro-tetrahydro-furan-2-ylmethyl ester (125542-16-7) + 6-chloro-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine (109304-00-9) + Benzoic acid (2R,3R,4S,5S)-3-acetoxy-5-(6-chloro-purin-9-yl)-4-fluoro-tetrahydro-furan-2-ylmethyl ester (125542-15-6)

Guidance literature:

With 4 A molecular sieve; In dichloromethane; for 15h; Yields of byproduct given; Heating;

DOI:10.1021/jm00165a015

upstream raw materials:

1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide

6-chloropurine

1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose

Downstream raw materials:

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)purine

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)purine-6-thiol

2'-F-ara-ddI

9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine