Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Base Information

• Chemical Name: Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
• CAS No.: 79171-98-5
• Molecular Formula: C₃₀H₂₈O₆
• Molecular Weight: 484.549

Synonyms:Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Chemical Property of Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Chemical Property:

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Technology Process of Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

There total 3 articles about Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl 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: 25.0%

Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxy-but-1-enyl)-hexahydro-cyclopenta[b]furan-5-yl ester (79171-99-6) → Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(S)-3-hydroxy-4-phenoxy-but-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (114488-93-6) + Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (79171-98-5)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; for 0.5h;

DOI:10.1021/jm00143a018

Reference yield:

methyl 2-phenoxyacetate (2065-23-8) → Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (79171-98-5)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / -78 °C

2: 1.) NaH / 1.) THF, 90 min, 2.) THF, 30 min

3: 25 percent / lithium triethylborohydride / tetrahydrofuran / 0.5 h

With sodium hydride; lithium triethylborohydride; In tetrahydrofuran;

DOI:10.1021/jm00143a018

Reference yield:

dimethyl (3-phenoxy-2-oxopropyl)phosphonate (40665-68-7) → Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (79171-98-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) THF, 90 min, 2.) THF, 30 min

2: 25 percent / lithium triethylborohydride / tetrahydrofuran / 0.5 h

With sodium hydride; lithium triethylborohydride; In tetrahydrofuran;

DOI:10.1021/jm00143a018

upstream raw materials:

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

methyl 2-phenoxyacetate

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Downstream raw materials:

(3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-hexahydro-cyclopenta[b]furan-2-one

N-(methanesulfonyl)-16-phenox-ω-tetranor-PGF_2α-carboxamide

(3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

(3aR,4R,5R,6aS)-Hexahydro-4-<(E)-(3R)-4-phenoxy-3-<(tetrahydro-2H-pyran-2-yl)oxy>-1-butenyl>-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-2-one

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