(3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate
• CAS No.: 64927-55-5
• Molecular Formula: C₂₂H₂₆F₂O₅
• Molecular Weight: 408.442
• Mol file: 64927-55-5.mol

Synonyms:(3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Chemical Property of (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

There total 3 articles about (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate 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:

(3aR,4R,5R,6aS)-4-((E)-4,4-difluoro-3-oxooct-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate → (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate (64927-55-5)

Guidance literature:

(3aR,4R,5R,6aS)-4-((E)-4,4-difluoro-3-oxooct-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate; With pyrographite; In ethyl acetate; at 25 - 40 ℃; for 2h;

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 - 25 ℃; under 1034.32 - 1292.9 Torr; Inert atmosphere;

Reference yield:

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one (39746-00-4,172821-93-1) → (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate (64927-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Dess-Martin periodane / dichloromethane / 5 h / 0 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

2.2: 0.5 h / 26 °C / Inert atmosphere

2.3: 20 h / 25 - 45 °C

3.1: pyrographite / ethyl acetate / 2 h / 25 - 40 °C

3.2: 20 - 25 °C / 1034.32 - 1292.9 Torr / Inert atmosphere

With sodium hydride; pyrographite; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; ethyl acetate; mineral oil;

Reference yield:

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (39746-01-5) → (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate (64927-55-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 26 °C / Inert atmosphere

1.3: 20 h / 25 - 45 °C

2.1: pyrographite / ethyl acetate / 2 h / 25 - 40 °C

2.2: 20 - 25 °C / 1034.32 - 1292.9 Torr / Inert atmosphere

With sodium hydride; pyrographite; In tetrahydrofuran; ethyl acetate; mineral oil;

upstream raw materials:

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

Downstream raw materials:

(Z)-7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid

(Z)-benzyl 7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoate

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