3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl azide

Base Information

• Chemical Name: 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl azide
• CAS No.: 371776-73-7
• Molecular Formula: C₁₉H₁₆FN₃O₅
• Molecular Weight: 385.352
• Mol file: 371776-73-7.mol

Synonyms:3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl azide

Chemical Property of 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl azide

There total 5 articles about 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl azide 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: 57.0%

1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose (171866-29-8) → 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl azide (371776-73-7) + 3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl azide (371776-79-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1515/znb-2001-0814

Reference yield:

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranose (171721-00-9) → 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl azide (371776-73-7)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr; AcOH / CH₂Cl₂ / 20 °C

2: 20 percent / NaN₃ / dimethylformamide / 5 h / 20 °C

With sodium azide; hydrogen bromide; acetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1515/znb-2001-0814

Reference yield:

1,3,5-tri-O-benzoyl-2-O-(2-imidazolylsulfonyl)-α-L-ribofuranose (171720-99-3) → 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl azide (371776-73-7)

Guidance literature:

Multi-step reaction with 3 steps

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

2: HBr; AcOH / CH₂Cl₂ / 20 °C

3: 20 percent / NaN₃ / dimethylformamide / 5 h / 20 °C

With sodium azide; 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-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose

1,3,5-Tri-O-benzoyl-α-L-ribofuranose

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

1,3,5-tri-O-benzoyl-2-O-(2-imidazolylsulfonyl)-α-L-ribofuranose

Downstream raw materials:

ethyl 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl)-1,2,3-triazole-5-carboxylate

ethyl 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl)-1,2,3-triazole-4-carboxylate