1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose

Base Information

• Chemical Name: 1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose
• CAS No.: 171866-29-8
• Molecular Formula: C₁₉H₁₆BrFO₅
• Molecular Weight: 423.235
• Mol file: 171866-29-8.mol

Synonyms:1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose

Chemical Property of 1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose

There total 25 articles about 1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose 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: 100.0%

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranose (171721-00-9) → 1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose (171866-29-8)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1021/jm960098l

Reference yield: 75.6%

1-O-acetyl-2,3,5-tri-O-benzoyl-α-L-ribofuranose (1173695-22-1) → 1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose (171866-29-8)

Guidance literature:

1-O-acetyl-2,3,5-tri-O-benzoyl-α-L-ribofuranose; With tetrabutyl ammonium fluoride; hydrogen bromide; In tetrahydrofuran; water; for 3h; Cooling with ice; Green chemistry;

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; water; for 3h; Solvent; Green chemistry;

Reference yield:

1,3,5-Tri-O-benzoyl-α-L-ribofuranose (171866-30-1) → 1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose (171866-29-8)

Guidance literature:

Multi-step reaction with 4 steps

1: SO₂Cl₂ / CH₂Cl₂; dimethylformamide / 3.5 h / -40 - 20 °C

2: 21.0 g / CH₂Cl₂; dimethylformamide / 15 h / 20 °C

3: 64 percent / aq. HF; KHF₂ / various solvent(s) / 1 h / 160 °C

4: HBr; AcOH / CH₂Cl₂ / 20 °C

With sulfuryl dichloride; potassium hydrogen bifluoride; hydrogen fluoride; hydrogen bromide; acetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1515/znb-2001-0814

upstream raw materials:

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranose

1-O-methyl-2-deoxy-2-fluoro-3,5-di-O-benzoyl-L-arabinofuranoside

benzoyl chloride

1-O-methyl-2-deoxy-2-fluoro-L-arabinofuranoside

Downstream raw materials:

1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-ethyluracil

N⁴-benzoyl-1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)cytosine

N⁴-benzoyl-1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-iodocytosine

1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)thymine