(3aS,3bR,4R,7aS,8aS)-octahydro-2H-furo[3′,2′:4,5]furo[2,3-c]-pyran-4-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl)carbamate

Base Information

• Chemical Name: (3aS,3bR,4R,7aS,8aS)-octahydro-2H-furo[3′,2′:4,5]furo[2,3-c]-pyran-4-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl)carbamate
• CAS No.: 1450609-03-6
• Molecular Formula: C₃₁H₄₂N₂O₉S
• Molecular Weight: 618.748
• Mol file: 1450609-03-6.mol

Synonyms:

Chemical Property of (3aS,3bR,4R,7aS,8aS)-octahydro-2H-furo[3′,2′:4,5]furo[2,3-c]-pyran-4-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,3bR,4R,7aS,8aS)-octahydro-2H-furo[3′,2′:4,5]furo[2,3-c]-pyran-4-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl)carbamate

There total 5 articles about (3aS,3bR,4R,7aS,8aS)-octahydro-2H-furo[3′,2′:4,5]furo[2,3-c]-pyran-4-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl)carbamate 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: 82.0%

4-nitrophenyl ((3aR,3bR,4R,7aS,8aS)-octahydro-5H-furo-[3′,2′:4,5]furo[2,3-c]pyran-4-yl)carbonate (1450608-97-5) + N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide (159005-71-7) → (3aS,3bR,4R,7aS,8aS)-octahydro-2H-furo[3′,2′:4,5]furo[2,3-c]-pyran-4-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl)carbamate (1450609-03-6)

Guidance literature:

With triethylamine; In acetonitrile; Inert atmosphere;

DOI:10.1021/jm400768f

Reference yield:

octahydro-2H-furo[3′,2′:4,5]furo[2,3-c]pyran-4-ol → (3aS,3bR,4R,7aS,8aS)-octahydro-2H-furo[3′,2′:4,5]furo[2,3-c]-pyran-4-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl)carbamate (1450609-03-6)

Guidance literature:

Multi-step reaction with 3 steps

1: lipase amano PS-30 / tetrahydrofuran / 20 h / 23 °C / Inert atmosphere

2: pyridine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

3: triethylamine / acetonitrile / Inert atmosphere

With pyridine; lipase amano PS-30; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jm400768f

Reference yield:

3,3a,7,8a-tetrahydro-2H-furo[3′,2′:4,5]furo[2,3-c]pyran-4(5H)-one → (3aS,3bR,4R,7aS,8aS)-octahydro-2H-furo[3′,2′:4,5]furo[2,3-c]-pyran-4-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl)carbamate (1450609-03-6)

Guidance literature:

Multi-step reaction with 5 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 12 h / 760.05 Torr / Inert atmosphere

2: L-Selectride / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

3: lipase amano PS-30 / tetrahydrofuran / 20 h / 23 °C / Inert atmosphere

4: pyridine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

5: triethylamine / acetonitrile / Inert atmosphere

With pyridine; palladium 10% on activated carbon; lipase amano PS-30; hydrogen; L-Selectride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1021/jm400768f

upstream raw materials:

C₉H₁₄O₄

4-nitrophenyl ((3aR,3bR,4R,7aS,8aS)-octahydro-5H-furo-[3′,2′:4,5]furo[2,3-c]pyran-4-yl)carbonate

N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide