4,7-difluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-imidazo[4,5-c]pyridine

Base Information

• Chemical Name: 4,7-difluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-imidazo[4,5-c]pyridine
• CAS No.: 855006-73-4
• Molecular Formula: C₃₂H₂₃F₂N₃O₇
• Molecular Weight: 599.547
• Mol file: 855006-73-4.mol

Synonyms:4,7-difluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-imidazo[4,5-c]pyridine

Chemical Property of 4,7-difluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-imidazo[4,5-c]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,7-difluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-imidazo[4,5-c]pyridine

There total 8 articles about 4,7-difluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-imidazo[4,5-c]pyridine 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: 70.0%

1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose (22224-38-0) + 4,7-difluoro-imidazo[4,5-c]pyridine (855006-72-3) → 4,7-difluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-imidazo[4,5-c]pyridine (855006-73-4)

Guidance literature:

4,7-difluoro-imidazo[4,5-c]pyridine; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; for 3h; Heating;

1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose; With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2005.03.190

Reference yield: 12.0%

1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose (22224-38-0) + 4,7-difluoro-imidazo[4,5-c]pyridine (855006-72-3) → 4,7-difluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-imidazo[4,5-c]pyridine (855006-73-4) + 4,7-difluoro-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-imidazo[4,5-c]pyridine

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2005.03.190

Reference yield:

3-chloro-2,4,5,6-tetrafluoropyridine (1735-84-8) → 4,7-difluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-imidazo[4,5-c]pyridine (855006-73-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 100 percent / CH₂Cl₂; dimethylformamide / 24 h / 40 °C

2.1: 83 percent / acetonitrile / 0.5 h / Heating

3.1: 95 percent / trifluoroacetic acid / 6 h / 70 °C

4.1: 100 percent / tert-butyl nitrite / tetrahydrofuran / 10 h / 60 °C

5.1: 84 percent / aq. ammonium hydroxide / 1.5 h / 20 °C

6.1: 86 percent / triethylamine; H₂ / Pd/C / ethanol / 24 h / 2585.74 Torr

7.1: 73 percent / potassium nitrate; sulfuric acid / 1.42 h / 4 - 20 °C

8.1: 87 percent / sulfuric acid / 24 h / 20 °C

9.1: 95 percent / H₂ / Raney nickel / ethanol / 3 h / 1861.73 Torr

10.1: 78 percent / 1.5 h / 100 °C

11.1: 1,1,1,3,3,3-hexamethyldisilazane; ammonium sulfate / 3 h / Heating

11.2: 70 percent / TMSOTf / 1,2-dichloro-ethane / 24 h / 20 °C

With ammonium hydroxide; ammonium sulfate; tert.-butylnitrite; sulfuric acid; hydrogen; potassium nitrate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; palladium on activated charcoal; nickel; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tetlet.2005.03.190

upstream raw materials:

1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose

4,7-difluoro-imidazo[4,5-c]pyridine

N-(3-chloro-2,5-difluoropyridin-4-yl)phthalimide

N-(3-chloro-2,5,6-trifluoropyridin-4-yl)phthalimide

Downstream raw materials:

3-deaza-3-fluoro-adenosine

Refernces