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

Base Information

• Chemical Name: 1-((2R,3R,5S)-3-Benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-5-methoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid methyl ester
• CAS No.: 233684-85-0
• Molecular Formula: C₂₆H₂₅N₃O₉
• Molecular Weight: 523.499
• Mol file: 233684-85-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

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) → 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 4 steps

1: NaOMe / methanol / 23 °C

2: NH₃ / methanol / 24 h / 23 °C

3: 57 percent / Et₃N / DMAP / acetonitrile / 23 °C

4: 5 percent / (CF₃CO)2O; pyridine / tetrahydrofuran / -12 - -2 °C

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

DOI:10.1055/s-1999-2755

upstream raw materials:

3-oxopentanedioic acid dimethyl ester

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