CHEMPACIFIC 59929

Base Information

• Chemical Name: CHEMPACIFIC 59929
• CAS No.: 856240-62-5
• Molecular Formula: C18H24O4
• Molecular Weight: 304.386
• Mol file: 856240-62-5.mol

Synonyms:CHEMPACIFIC 59929;2H-CYCLOPENTA[B]FURAN-2,5-DIOL, HEXAHYDRO-4-[(1E,3S)-3-HYDROXY-5-PHENYL-1-PENTENYL]-, (3AR,4R,5R,6AS)-;2H-Cyclopenta[b]furan-2,5-diol, hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-, (3aR,4R,5R,6aS)-

Chemical Property of CHEMPACIFIC 59929

Chemical Property:

• Boiling Point: 506.7±50.0 °C(Predicted)
• PKA: 13.05±0.60(Predicted)
• PSA: 69.92000
• Density: 1.292±0.06 g/cm3(Predicted)
• LogP: 1.64060

Purity/Quality:

98% min ^*data from raw suppliers

(3aR,4R,5R,6aS)-4-((S,E)-3-Hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol(BimatoprostImpurity) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (3aR,4R,5R,6aS)-4-((S,E)-3-Hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol is the impurity in the synthesis of bimatoprost (B386800), an antiglaucoma drug and analog of prostaglandin.

Technology Process of CHEMPACIFIC 59929

There total 38 articles about CHEMPACIFIC 59929 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: 89.0%

(3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-ol (1395619-18-7) → (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol (856240-62-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; water; at 0 ℃; for 4h;

Reference yield: 81.0%

(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) → (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol (856240-62-5)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -70 ℃; for 2h;

Reference yield:

1-bromo-4-phenylbutan-2-one (31984-10-8) → (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol (856240-62-5)

Guidance literature:

Multi-step reaction with 5 steps

1: acetonitrile / 1 h / 80 °C

2: lithium chloride; triethylamine / tetrahydrofuran / 2 h / -4 - 20 °C

3: (-)-diisopinocamphenylborane chloride / dichloromethane / 26 h / -25 - 30 °C

4: potassium carbonate / methanol / 2 h / 25 °C

5: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -70 °C

With diisobutylaluminium hydride; potassium carbonate; triethylamine; (-)-diisopinocamphenylborane chloride; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2: |Horner-Wadsworth-Emmons Olefination;

upstream raw materials:

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

(3aR,4R,5R,6aS)-4-[3S-(p-nitrobenzoyloxy)-5-phenyl-1E-pentenyl]-5-(benzoyloxy)-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

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one

Downstream raw materials:

(5E)-N-ethyl-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]-cyclopentyl]hept-5-enamide

bimatoprost

(5Z)-bimatoprost acid

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