3-deoxy-2,5-di-O-benzoyl-β-D-erythro-pentofuranosyl azide

Base Information

• Chemical Name: 3-deoxy-2,5-di-O-benzoyl-β-D-erythro-pentofuranosyl azide
• CAS No.: 233684-78-1
• Molecular Formula: C₁₉H₁₇N₃O₅
• Molecular Weight: 367.361
• Mol file: 233684-78-1.mol

Synonyms:3-deoxy-2,5-di-O-benzoyl-β-D-erythro-pentofuranosyl azide

Chemical Property of 3-deoxy-2,5-di-O-benzoyl-β-D-erythro-pentofuranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-deoxy-2,5-di-O-benzoyl-β-D-erythro-pentofuranosyl azide

There total 1 articles about 3-deoxy-2,5-di-O-benzoyl-β-D-erythro-pentofuranosyl 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: 86.0%

methyl 3-deoxy-2,5-di-O-benzoyl-β-D-erythro-pentofuranoside (4395-37-3) → 3-deoxy-2,5-di-O-benzoyl-β-D-erythro-pentofuranosyl azide (233684-78-1) + 3-deoxy-2,5-di-O-benzoyl-α-D-erythro-pentofuranosyl azide

Guidance literature:

With trimethylsilylazide; tin(IV) chloride; In dichloromethane; at 23 ℃; for 12h;

DOI:10.1016/S0008-6215(99)00293-1

Reference yield: 93.0%

3-oxopentanedioic acid dimethyl ester (1830-54-2) + 3-deoxy-2,5-di-O-benzoyl-β-D-erythro-pentofuranosyl azide (233684-78-1) → 1-((2R,3R,5S)-3-Benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-5-methoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid methyl ester (233684-85-0)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 45 ℃; for 38h;

DOI:10.1055/s-1999-2755

Reference yield:

3-deoxy-2,5-di-O-benzoyl-β-D-erythro-pentofuranosyl azide (233684-78-1) → Acetic acid (2R,3R,5S)-5-acetoxymethyl-2-(4-cyano-5-cyanomethyl-[1,2,3]triazol-1-yl)-tetrahydro-furan-3-yl ester

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / K₂CO₃ / dimethylsulfoxide / 38 h / 45 °C

2: NaOMe / methanol / 23 °C

3: NH₃ / methanol / 24 h / 23 °C

4: 57 percent / Et₃N / DMAP / acetonitrile / 23 °C

5: 5 percent / (CF₃CO)2O; pyridine / tetrahydrofuran / -12 - -2 °C

With pyridine; ammonia; sodium methylate; potassium carbonate; triethylamine; trifluoroacetic anhydride; dmap; In tetrahydrofuran; methanol; dimethyl sulfoxide; acetonitrile; 1: Cycloaddition / 2: Hydrolysis / 3: Substitution / 4: Acetylation / 5: Dehydration;

DOI:10.1055/s-1999-2755

upstream raw materials:

methyl 3-deoxy-2,5-di-O-benzoyl-β-D-erythro-pentofuranoside

Downstream raw materials:

1-((2R,3R,5S)-3-Benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-5-methoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid methyl ester

Refernces