4-acetoxy-5-(acetylamino)-2-{4-[(3-carboxypropionyl)amino]-2-(difluoromethyl)phenoxy}-6-(1,2,3-triacetoxypropyl)tetrahydropyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: 4-acetoxy-5-(acetylamino)-2-{4-[(3-carboxypropionyl)amino]-2-(difluoromethyl)phenoxy}-6-(1,2,3-triacetoxypropyl)tetrahydropyran-2-carboxylic acid methyl ester
• CAS No.: 873014-24-5
• Molecular Formula: C₃₁H₃₈F₂N₂O₁₆
• Molecular Weight: 732.643
• Mol file: 873014-24-5.mol

Synonyms:4-acetoxy-5-(acetylamino)-2-{4-[(3-carboxypropionyl)amino]-2-(difluoromethyl)phenoxy}-6-(1,2,3-triacetoxypropyl)tetrahydropyran-2-carboxylic acid methyl ester

Chemical Property of 4-acetoxy-5-(acetylamino)-2-{4-[(3-carboxypropionyl)amino]-2-(difluoromethyl)phenoxy}-6-(1,2,3-triacetoxypropyl)tetrahydropyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-acetoxy-5-(acetylamino)-2-{4-[(3-carboxypropionyl)amino]-2-(difluoromethyl)phenoxy}-6-(1,2,3-triacetoxypropyl)tetrahydropyran-2-carboxylic acid methyl ester

There total 5 articles about 4-acetoxy-5-(acetylamino)-2-{4-[(3-carboxypropionyl)amino]-2-(difluoromethyl)phenoxy}-6-(1,2,3-triacetoxypropyl)tetrahydropyran-2-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: 94.0%

methyl {2-O-[2-(difluoromethyl)-4-aminophenyl]-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-galacto-2-nonulopyranosid}onate (873014-23-4) + succinic acid anhydride (108-30-5) → 4-acetoxy-5-(acetylamino)-2-{4-[(3-carboxypropionyl)amino]-2-(difluoromethyl)phenoxy}-6-(1,2,3-triacetoxypropyl)tetrahydropyran-2-carboxylic acid methyl ester (873014-24-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1002/anie.200501738

Reference yield:

methyl [2-O-(2-formyl-4-nitrophenyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-galacto-2-nonulopyranosid]onate (864933-92-6) → 4-acetoxy-5-(acetylamino)-2-{4-[(3-carboxypropionyl)amino]-2-(difluoromethyl)phenoxy}-6-(1,2,3-triacetoxypropyl)tetrahydropyran-2-carboxylic acid methyl ester (873014-24-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 47 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂

2: 95 percent / hydrogen / Pd/C / methanol

3: 94 percent / triethylamine / CH₂Cl₂ / 3 h / 20 °C

With diethylamino-sulfur trifluoride; hydrogen; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1002/anie.200501738

Reference yield:

methyl {2-O-[2-(difluoromethyl)-4-nitrophenyl]-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid}onate (864933-93-7) → 4-acetoxy-5-(acetylamino)-2-{4-[(3-carboxypropionyl)amino]-2-(difluoromethyl)phenoxy}-6-(1,2,3-triacetoxypropyl)tetrahydropyran-2-carboxylic acid methyl ester (873014-24-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / hydrogen / Pd/C / methanol

2: 94 percent / triethylamine / CH₂Cl₂ / 3 h / 20 °C

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1002/anie.200501738

upstream raw materials:

methyl {2-O-[2-(difluoromethyl)-4-aminophenyl]-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-galacto-2-nonulopyranosid}onate

succinic acid anhydride

methyl [2-O-(2-formyl-4-nitrophenyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-galacto-2-nonulopyranosid]onate

methyl {2-O-[2-(difluoromethyl)-4-nitrophenyl]-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid}onate

Downstream raw materials:

4-acetoxy-5-(acetylamino)-2-[2-(difluoromethyl)-4-(3-{6-[5-(2-oxohexahydrothieno[3,4-d]imidazol-6-yl)pentanoylamino]hexylcarbamoyl}propionylamino)phenoxy]-6-(1,2,3-triacetoxypropyl)tetrahydropyran-2-carboxylic acid methyl ester