2-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-chloro-β-D-arabinofuranosyl)-adenine

Base Information

• Chemical Name: 2-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-chloro-β-D-arabinofuranosyl)-adenine
• CAS No.: 1093278-65-9
• Molecular Formula: C₂₄H₁₉Cl₂N₅O₅
• Molecular Weight: 528.351
• Mol file: 1093278-65-9.mol

Synonyms:2-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-chloro-β-D-arabinofuranosyl)-adenine

Chemical Property of 2-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-chloro-β-D-arabinofuranosyl)-adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-chloro-β-D-arabinofuranosyl)-adenine

There total 9 articles about 2-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-chloro-β-D-arabinofuranosyl)-adenine 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: 44.4%

2-chloro-9-(3',5'-di-O-benzoyl-2'-O-trifluoromethylsulfonyl-β-D-ribofuranosyl)adenine (1353040-43-3) → 2-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-chloro-β-D-arabinofuranosyl)-adenine (1093278-65-9) + 6-amino-2-chloro-9-(2'-deoxy-2'-fluoro-3',5'-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purine (355138-50-0)

Guidance literature:

With guanidine hydrogen carbonate; triethylamine hydrofluoride; In ethyl acetate; at 20 - 80 ℃; Product distribution / selectivity;

Reference yield: 36.0%

C19H16BrClO5 (1093278-48-8) + 2-chloroadenine (1839-18-5) → 2-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-chloro-β-D-arabinofuranosyl)-adenine (1093278-65-9)

Guidance literature:

With calcium hydride; potassium tert-butylate; In tert-Amyl alcohol; 1,2-dichloro-ethane; acetonitrile; at 50 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/op800182x

Reference yield:

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → 2-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-chloro-β-D-arabinofuranosyl)-adenine (1093278-65-9)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / dichloromethane / 2.78 h / -30 - -4 °C / Inert atmosphere

2: lithium chloride / 1-methyl-pyrrolidin-2-one / 17.5 h / 20 °C / Inert atmosphere

3: hydrogen bromide; acetic acid / dichloromethane / 17 h / 20 °C / Inert atmosphere

4: calcium hydride; potassium tert-butylate / acetonitrile; 1,2-dichloro-ethane; tert-Amyl alcohol / 1.5 h / 50 °C / Inert atmosphere

With pyridine; calcium hydride; potassium tert-butylate; hydrogen bromide; acetic acid; lithium chloride; In 1-methyl-pyrrolidin-2-one; tert-Amyl alcohol; dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/op800182x

upstream raw materials:

2-chloro-9-(3',5'-di-O-benzoyl-2'-O-trifluoromethylsulfonyl-β-D-ribofuranosyl)adenine

2-chloro-9-(3',5'-di-O-benzoyl-β-D-ribofuranosyl)adenine

6-amino-2-chloro-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose