4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

Base Information

• Chemical Name: 4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine
• CAS No.: 174019-77-3
• Molecular Formula: C₂₆H₁₉BrFN₅O₅
• Molecular Weight: 580.37
• Mol file: 174019-77-3.mol

Synonyms:4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

Chemical Property of 4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

There total 3 articles about 4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)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:

methyl 5-deoxy-5-fluoro-2,3-di-O-benzoyl-β-D-ribofuranoside (174174-99-3) → 4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine (174019-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / H₂SO₄ / acetic acid / 1.) 0 deg C, 1 h, 2.) room temperature, 22 h

2: 1.) HMDS, Me₃SiCl, 2.) TMSTf / 1.) xylene, reflux, 18 h, 2.) 1,2-dichloroethane, room temperature, overnight

With chloro-trimethyl-silane; TMSTf; sulfuric acid; 1,1,1,3,3,3-hexamethyl-disilazane; In acetic acid;

DOI:10.1080/15257779508010707

Reference yield:

methyl 5-deoxy-5-fluoro-β-D-ribofuranoside (151266-35-2) → 4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine (174019-77-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / pyridine / Ambient temperature

2: 78 percent / H₂SO₄ / acetic acid / 1.) 0 deg C, 1 h, 2.) room temperature, 22 h

3: 1.) HMDS, Me₃SiCl, 2.) TMSTf / 1.) xylene, reflux, 18 h, 2.) 1,2-dichloroethane, room temperature, overnight

With pyridine; chloro-trimethyl-silane; TMSTf; sulfuric acid; 1,1,1,3,3,3-hexamethyl-disilazane; In acetic acid;

DOI:10.1080/15257779508010707

Reference yield:

4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine (19393-83-0) + 1-O-acetyl-2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranoside (174019-76-2) → 4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine (174019-77-3)

Guidance literature:

With chloro-trimethyl-silane; TMSTf; 1,1,1,3,3,3-hexamethyl-disilazane; Yield given. Multistep reaction; 1.) xylene, reflux, 18 h, 2.) 1,2-dichloroethane, room temperature, overnight;

DOI:10.1080/15257779508010707

upstream raw materials:

4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine

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

methyl 5-deoxy-5-fluoro-2,3-di-O-benzoyl-β-D-ribofuranoside

methyl 5-deoxy-5-fluoro-β-D-ribofuranoside

Downstream raw materials:

4-amino-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

C₂₆H₂₂FN₅O₅S