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

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-5-Hydroxy-4-((R)-3-hydroxy-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2-one
• CAS No.: 145667-75-0
• Molecular Formula: C18H24O4
• Molecular Weight: 304.386
• European Community (EC) Number: 689-784-9
• DSSTox Substance ID: DTXSID30437648
• Wikidata: Q72487240
• Mol file: 145667-75-0.mol

Synonyms:145667-75-0;(3aR,4R,5R,6aS)-5-Hydroxy-4-((R)-3-hydroxy-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2-one;Latanoprost Lactone Diol;(3aR,4R,5R,6aS)-5-hydroxy-4-[(3R)-3-hydroxy-5-phenylpentyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one;(3AR,4R,5R,6aS)-5-Hydroxy-4-((R)-3-hydroxy-5-phenyl-pentyl)hexahydro-2H-cyclopenta[b]furan-2-one;(1S,5R,6R,7R)-6-[(3R)-3-hydroxy-5-phenyl-1-pentyl]-7(R)-hydroxy-2-oxabicyclo[3.3.0]octan-3-one;145773-21-3;SCHEMBL12190696;DTXSID30437648;HMS3649I19;AKOS015896624;(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(3R)-3-hydroxy-5-phenylpentyl]2H-cyclopenta[b]furan-2-one;AC-24760;HY-125946;CS-0103245;SR-01000946576;J-501156;SR-01000946576-1;(3aR,4R,5R,6aS)-5-Hydroxy-4-[(3R)-3-hydroxy-5-phenylpentyl]hexahydro-2H-cyclopenta[b]furan-2-one;(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-((R)-3-hydroxy-5-phenylpentyl)cyclopenta[b]furan-2-one

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

Chemical Property:

• Appearance/Colour: White or almost white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 69-71 °C
• Refractive Index: 1.568
• Boiling Point: 522.959 °C at 760 mmHg
• PKA: 14.58±0.40(Predicted)
• Flash Point: 190.276 °C
• PSA: 66.76000
• Density: 1.202 g/cm³
• LogP: 2.07280
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 304.16745924
• Heavy Atom Count: 22
• Complexity: 377

Purity/Quality:

97% ^*data from raw suppliers

(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(3R)-3-hydroxy-5-phenylpentyl]2H-cyclopenta[b]furan-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C2C1OC(=O)C2)CCC(CCC3=CC=CC=C3)O)O
• Isomeric SMILES: C1[C@H]([C@@H]([C@@H]2[C@H]1OC(=O)C2)CC[C@H](CCC3=CC=CC=C3)O)O
• Uses: (3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(3R)-3-hydroxy-5-phenylpentyl]2H-cyclopenta[b]furan-2-one is phenyl-substituted prostaglandin and a potent and selective antiglaucoma agents.

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

There total 27 articles about (3aR,4R,5R,6aS)-5-Hydroxy-4-((R)-3-hydroxy-5-phenylpentyl)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: 100.0%

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one (41639-74-1) → (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one (145667-75-0)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; sodium hydroxide; In ethanol; at 20 ℃; for 5h; under 760.051 Torr;

DOI:10.1002/anie.201902371

Reference yield: 88.5%

C18H22O4 → (3aR,4R,5R,6aS)-5-hydroxy-4-(5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2-one + (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one (145667-75-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 2h; under 2280.15 Torr;

DOI:10.1039/c9nj01186b

Reference yield: 83.6%

(1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one (145667-74-9) → (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one (145667-75-0)

Guidance literature:

With potassium carbonate; In methanol; for 6h; Ambient temperature;

DOI:10.1021/jm00054a008

upstream raw materials:

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

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

benzyl bromide

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

Downstream raw materials:

latanoprost

latanoprost acid

(3aR,4R,5R,6aS)-4-((3R)-5-phenyl-3-((tetrahydro-2H-pyran-2-yl)oxy)pentyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((R)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2-one