[(3aR,4R,5R,6aS)-4-[(E,3S)-3-Hydroxy-5-phenylpent-1-enyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-Phenylbenzoate

Base Information

• Chemical Name: [(3aR,4R,5R,6aS)-4-[(E,3S)-3-Hydroxy-5-phenylpent-1-enyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-Phenylbenzoate
• CAS No.: 41639-73-0
• Molecular Formula: C31H30O5
• Molecular Weight: 482.576
• European Community (EC) Number: 682-026-8
• Wikidata: Q76415443
• Mol file: 41639-73-0.mol

Synonyms:41639-73-0;[(3aR,4R,5R,6aS)-4-[(E,3S)-3-Hydroxy-5-phenylpent-1-enyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-Phenylbenzoate;(3aR,4R,5R,6aS)-Hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2-oxo-2H-cyclopenta[b]furan-5;SCHEMBL5375829;(3AR,4R,5R,6AS)-4-((S,E)-3-hydroxy-5-phenylpent-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate;(3AR,4R,5R,6AS)-4-((S,E)-3-hydroxy-5-phenylpent-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl[1,1'-biphenyl]-4-carboxylate;(3aR,4R,5R,6aS)-Hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl Ester [1,1'-Biphenyl]-4-carboxylic Acid;(3aR,4R,5R,6aS)-hexahydro-4-[(3S)-3-hydroxy-5-phenyl-1E-pentenyl]-5-(p-phenylbenzoyloxy)-2H-cyclopenta[b]furan-2-one

Chemical Property of [(3aR,4R,5R,6aS)-4-[(E,3S)-3-Hydroxy-5-phenylpent-1-enyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-Phenylbenzoate

Chemical Property:

• PSA: 72.83000
• LogP: 5.38050
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 482.20932405
• Heavy Atom Count: 36
• Complexity: 757

Purity/Quality:

98% ^*data from raw suppliers

(3aR,4R,5R,6aS)-Hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-ylEster[1,1''-Biphenyl]-4-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C2C(CC(=O)O2)C(C1OC(=O)C3=CC=C(C=C3)C4=CC=CC=C4)C=CC(CCC5=CC=CC=C5)O
• Isomeric SMILES: C1[C@H]2[C@H](CC(=O)O2)[C@H]([C@@H]1OC(=O)C3=CC=C(C=C3)C4=CC=CC=C4)/C=C/[C@H](CCC5=CC=CC=C5)O
• Uses: [1,1'-Biphenyl]-4-carboxylic acid, (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl] -2-oxo-2H-cyclopenta[b]furan-5-yl ester is an impurity of Latanoprost (L177280), a prostaglandin analogue used to treat glaucoma and other degenerative diseases of the eye. Latanoprost Enol is an impurity of Latanoprost (L177280), a prostaglandin analogue used to treat glaucoma and other degenerative diseases of the eye.

Technology Process of [(3aR,4R,5R,6aS)-4-[(E,3S)-3-Hydroxy-5-phenylpent-1-enyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-Phenylbenzoate

There total 16 articles about [(3aR,4R,5R,6aS)-4-[(E,3S)-3-Hydroxy-5-phenylpent-1-enyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-Phenylbenzoate 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: 86.0%

(1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one (41639-72-9) → (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one (41639-73-0)

Guidance literature:

(1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one; With (-)-B-chlorodiisopinocampheylborane; In dichloromethane; at -30 - -25 ℃;

With methanol; In dichloromethane; at 20 ℃; for 0.5h; Product distribution / selectivity;

Reference yield: 33.1%

(1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one (41639-72-9) → (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one (41639-23-0) + (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one (41639-73-0)

Guidance literature:

With L-Selectride; In tetrahydrofuran; diethyl ether; at -78 - -75 ℃; for 1h;

DOI:10.1021/jm00054a008

Reference yield:

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) → (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one (41639-73-0)

Guidance literature:

Multi-step reaction with 3 steps

1: DCC, phosphoric acid / 1,2-dimethoxy-ethane / a) 18 deg C, 30 min, b) RT, 2 h

2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h

3: 33.1 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C

With phosphoric acid; L-Selectride; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether;

DOI:10.1021/jm00054a008

upstream raw materials:

(1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one

(-)-Corey lactone 5-(4-phenylbenzoate)

benzyl bromide

(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

Downstream raw materials:

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

(1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one

(1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-ol

(1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one