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

Base Information

• Chemical Name: 6-amino-2-chloro-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine
• CAS No.: 1055168-98-3
• Molecular Formula: C₃₁H₂₄ClN₅O₇
• Molecular Weight: 614.014
• Mol file: 1055168-98-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 6-amino-2-chloro-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-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: 58.0%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + 2-chloroadenine (1839-18-5) → 6-amino-2-chloro-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine (1055168-98-3)

Guidance literature:

2-chloroadenine; With N,O-Bis(trimethylsilyl)trifluoroacetamide; In acetonitrile; for 1h; Reflux; Inert atmosphere;

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; With toluene-4-sulfonic acid; In acetonitrile; for 1h; Reflux; Inert atmosphere;

DOI:10.1016/j.bmc.2017.11.022

Reference yield:

2-Chloroadenosine (146-77-0) + benzoyl chloride (98-88-4) → 2-chloro-9-(3',5'-di-O-benzoyl-β-D-ribofuranosyl)adenine (1353040-42-2) + 6-amino-2-chloro-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine (1055168-98-3) + 2-chloro-9-(2',5'-di-O-benzoyl-β-D-ribofuranosyl)adenine (1353040-41-1)

Guidance literature:

With pyridine; In acetonitrile; at -5 - 5 ℃; for 0.5h;

Reference yield:

2-chloroadenine (1839-18-5) → 2-chloro-9-(3',5'-di-O-benzoyl-β-D-ribofuranosyl)adenine (1353040-42-2) + 6-amino-2-chloro-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine (1055168-98-3)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; potassium dihydrogenphosphate; potassium hydroxide / water; dimethyl sulfoxide / 4 h / 58 - 61 °C / pH 7.1-7.2 / Enzymatic reaction

2: pyridine / acetonitrile / 0.5 h / -5 - 5 °C

With pyridine; hydrogenchloride; potassium dihydrogenphosphate; potassium hydroxide; In water; dimethyl sulfoxide; acetonitrile;

upstream raw materials:

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

2-chloroadenine

2-Chloroadenosine

benzoyl chloride

Downstream raw materials:

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

clofarabine

6-amino-2-chloro-9-(2'-deoxy-2'-fluoro-3',5'-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purine

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