(3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-3-hydroxy-4-(4-(hydroxymethyl)-N-isobutylphenylsulfonamido)-1-phenylbutan-2-yl carbamate

Base Information

• Chemical Name: (3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-3-hydroxy-4-(4-(hydroxymethyl)-N-isobutylphenylsulfonamido)-1-phenylbutan-2-yl carbamate
• CAS No.: 1262482-53-0
• Molecular Formula: C₂₉H₄₀N₂O₈S
• Molecular Weight: 576.711
• Mol file: 1262482-53-0.mol

Synonyms:(3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-3-hydroxy-4-(4-(hydroxymethyl)-N-isobutylphenylsulfonamido)-1-phenylbutan-2-yl carbamate

Chemical Property of (3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-3-hydroxy-4-(4-(hydroxymethyl)-N-isobutylphenylsulfonamido)-1-phenylbutan-2-yl carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-3-hydroxy-4-(4-(hydroxymethyl)-N-isobutylphenylsulfonamido)-1-phenylbutan-2-yl carbamate

There total 11 articles about (3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-3-hydroxy-4-(4-(hydroxymethyl)-N-isobutylphenylsulfonamido)-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: 72.0%

→ (3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-3-hydroxy-4-(4-(hydroxymethyl)-N-isobutylphenylsulfonamido)-1-phenylbutan-2-yl carbamate (1262482-53-0)

Guidance literature:

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-3-hydroxy-4-(4-(hydroxymethyl)-N-isobutylphenylsulfonamido)-1-phenylbutan-2-yl carbamate (1262482-53-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 1.5 h / 0 °C / Inert atmosphere

2.1: 2,4,6-trimethyl-pyridine / dichloromethane / 7 h / -78 °C / Inert atmosphere

3.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

4.1: potassium carbonate / methanol / 2 h / 23 °C

5.1: ozone / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

5.2: 2 h / 0 °C / Inert atmosphere

6.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 23 °C

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

9.1: triethylamine / acetonitrile / 0 - 23 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; triethylsilane; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium carbonate; ozone; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jm1012787

Reference yield:

C21H30N2O4S (1037666-14-0) + (3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate (1075209-47-0) → (3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-3-hydroxy-4-(4-(hydroxymethyl)-N-isobutylphenylsulfonamido)-1-phenylbutan-2-yl carbamate (1262482-53-0)

Guidance literature:

With triethylamine; In acetonitrile; at 0 - 23 ℃; Inert atmosphere;

DOI:10.1021/jm1012787

upstream raw materials:

C₂₆H₃₈N₂O₆S

C₂₁H₃₀N₂O₄S

(3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate

2R-(2-acetoxyethyl)-3-cyclopenten-1S-ol