7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-4-(furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Base Information

• Chemical Name: 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-4-(furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine
• CAS No.: 1338072-98-2
• Molecular Formula: C₂₉H₂₁F₂N₃O₆
• Molecular Weight: 545.499
• Mol file: 1338072-98-2.mol

Synonyms:7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-4-(furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Chemical Property of 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-4-(furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-4-(furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

There total 2 articles about 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-4-(furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine 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: 88.0%

4-chloro-7-(2-deoxy-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (909101-46-8) + 2-(tributylstannyl)furan (118486-94-5) → 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-4-(furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine (1338072-98-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 100 ℃; for 1h; Inert atmosphere;

DOI:10.1135/cccc2011082

Reference yield:

((2R,3R,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate (98855-71-1) → 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-4-(furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine (1338072-98-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Tris(3,6-dioxaheptyl)amine; potassium hydroxide / acetonitrile / 0.25 h / 20 °C

1.2: 0.17 h / 20 °C

2.1: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; Tris(3,6-dioxaheptyl)amine; potassium hydroxide; In N,N-dimethyl-formamide; acetonitrile; 2.1: Stille coupling;

DOI:10.1135/cccc2011082

upstream raw materials:

4-chloro-7-(2-deoxy-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine

2-(tributylstannyl)furan

((2R,3R,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate