5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide

Base Information

• Chemical Name: 5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide
• CAS No.: 136228-19-8
• Molecular Formula: C₁₂H₁₂BrFO₃
• Molecular Weight: 303.128
• Mol file: 136228-19-8.mol

Synonyms:5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide

Chemical Property of 5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide

There total 9 articles about 5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide 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:

5-O-Benzoyl-2,3-dideoxy-2-fluoro-1-O-methyl-β-D-threo-pentofuranose (136228-16-5) → 5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide (136228-19-8)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jm00090a008

Reference yield:

5-O-benzoyl-2,3-dideoxy-1,2-difluoro-α-D-arabinofuranose (153585-72-9) → 5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide (136228-19-8)

Guidance literature:

With hydrogen bromide; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/jm00032a017

Reference yield:

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate (4105-29-7) → 5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide (136228-19-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / H₂SO₄ / H₂O; dioxane / 4 h / 70 - 80 °C

2: 49.8 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 0 - 25 °C

3: 30percent HBr in AcOH / CH₂Cl₂ / 2 h / Ambient temperature

With diethylamino-sulfur trifluoride; sulfuric acid; hydrogen bromide; In 1,4-dioxane; dichloromethane; water;

DOI:10.1021/jm00032a017

upstream raw materials:

5-O-Benzoyl-2,3-dideoxy-2-fluoro-1-O-methyl-β-D-threo-pentofuranose

5-O-benzoyl-2,3-dideoxy-1,2-difluoro-α-D-arabinofuranose

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate

2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide

Downstream raw materials:

1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-5-fluorocytosine

1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)cytosine

1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)pyrimidin-2(H)-one

iodenosine