[3aR,4R(3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyoctyl)-hexahydro-2H-cyclopenta[b]furan-2-one

Base Information

• Chemical Name: [3aR,4R(3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyoctyl)-hexahydro-2H-cyclopenta[b]furan-2-one
• CAS No.: 69224-05-1
• Molecular Formula: C₂₂H₃₀O₅
• Molecular Weight: 374.477

Synonyms:[3aR,4R(3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyoctyl)-hexahydro-2H-cyclopenta[b]furan-2-one

Chemical Property of [3aR,4R(3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyoctyl)-hexahydro-2H-cyclopenta[b]furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of [3aR,4R(3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyoctyl)-hexahydro-2H-cyclopenta[b]furan-2-one

There total 2 articles about [3aR,4R(3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyoctyl)-hexahydro-2H-cyclopenta[b]furan-2-one 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%

[3aR,4R(1E,3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyocten-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-one (51705-58-9) → [3aR,4R(3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyoctyl)-hexahydro-2H-cyclopenta[b]furan-2-one (69224-05-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; atmospheric pressure;

DOI:10.1016/j.bmc.2004.04.034

Reference yield:

(3aR,4R,5R,6aS)-benzoic acid 2-oxo-4-[(1E)-3-oxo-oct-1-enyl]-hexahydro-cyclopenta[b]furan-5-yl ester (40834-86-4,185225-06-3) → [3aR,4R(3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyoctyl)-hexahydro-2H-cyclopenta[b]furan-2-one (69224-05-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / 0 °C

2: 94 percent / H₂ / Pd/C / ethyl acetate / atmospheric pressure

With (+)-β-chlorodiisopinocampheylborane; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/j.bmc.2004.04.034

Reference yield:

[3aR,4R(3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyoctyl)-hexahydro-2H-cyclopenta[b]furan-2-one (69224-05-1) → Benzoic acid (3aR,4R,5R,6aS)-4-((E)-oct-2-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester + [3aR,4R(3S),5R,6aS]-5-benzoyloxy-4-(3-fluorooctyl)-hexahydro-2H-cyclopenta[b]furan-2-one (733037-18-8)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane;

DOI:10.1016/j.bmc.2004.04.034

upstream raw materials:

[3aR,4R(1E,3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyocten-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-benzoic acid 2-oxo-4-[(1E)-3-oxo-oct-1-enyl]-hexahydro-cyclopenta[b]furan-5-yl ester

Downstream raw materials:

[3aR,4R(3S),5R,6aS]-5-benzoyloxy-4-(3-fluorooctyl)-hexahydro-2H-cyclopenta[b]furan-2-one

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