CLOPROSTENOL LACTONE DIOL

Base Information

• Chemical Name: CLOPROSTENOL LACTONE DIOL
• CAS No.: 53906-54-0
• Molecular Formula: C17H19ClO5
• Molecular Weight: 338.78
• Mol file: 53906-54-0.mol

Synonyms:2H-Cyclopenta[b]furan-2-one, 4-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxy-1-buten-1-yl]hexahydro-5-hydroxy-, (3aR,4R,5R,6aS)-;2H-Cyclopenta[b]furan-2-one, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-5-hydroxy-, [3aR-[3aα,4α(1E,3R*),5β,6aα]]-;

Chemical Property of CLOPROSTENOL LACTONE DIOL

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.648
• Boiling Point: 546.316 °C at 760 mmHg
• Flash Point: 284.202 °C
• PSA: 75.99000
• Density: 1.423 g/cm³
• LogP: 1.94840
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3AR,4R,5R,6aS)-4-((R,E)-4-(3-Chlorophenoxy)-3-hydroxybut-1-en-1-yl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CLOPROSTENOL LACTONE DIOL

There total 14 articles about CLOPROSTENOL LACTONE DIOL 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:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (3aR,4R,5R,6aS)-4-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-5-hydroxy-hexahydro-cyclopenta[b]furan-2-one (52267-81-9,53906-54-0,54142-65-3,59685-87-9,59685-90-4,72029-56-2,93302-71-7,93302-72-8)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂SO₄

2: MeONa / methanol

3: (COCl)2, NEt₃ / dimethylsulfoxide

4: 50percent aq. NaOH, BuNEt₃Cl / CH₂Cl₂

5: (i-Bu)2Al-O-C₆H₂-(2,6-di-t-Bu,4-Me) / CH₂Cl₂ / -78 °C

With sodium hydroxide; oxalyl dichloride; sulfuric acid; sodium methylate; triethylbutylammonium chloride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; triethylamine; In methanol; dichloromethane; dimethyl sulfoxide;

Reference yield:

(3aR,4R,5R,6aS)-4-((E)-4-(3-chlorophenoxy)-3-oxobut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1′-biphenyl]-4-carboxylate (54324-79-7) → (3aR,4R,5R,6aS)-4-((R,E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one (53906-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium triethylborohydride / tetrahydrofuran / 0.5 h

2: potassium carbonate / methanol; tetrahydrofuran / 2.5 h

With lithium triethylborohydride; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1021/jm00143a018

Reference yield:

(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (38754-71-1) → (3aR,4R,5R,6aS)-4-((R,E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one (53906-54-0)

Guidance literature:

Multi-step reaction with 3 steps

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

2: lithium triethylborohydride / tetrahydrofuran / 0.5 h

3: potassium carbonate / methanol; tetrahydrofuran / 2.5 h

With sodium hydride; lithium triethylborohydride; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1021/jm00143a018

upstream raw materials:

[3aα,4α(E),5β,6aα]-(+/-)-4-[4-(3-chlorophenoxy)-3-oxo-1-butenyl]-hexahydro-5-hydroxy-2H-cyclopenta[b]-furan-2-one

dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate

(3aR,4R,5R,6aS)-4-((E)-4-(3-chlorophenoxy)-3-oxobut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1′-biphenyl]-4-carboxylate

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

Downstream raw materials:

(1SR, 5RS, 6RS, 7RS)-7-tert-butyldimethylsilyloxy-6-<(3RS)-3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1(E)-en-1-yl>-2-oxabicyclo<3.3.0>octan-3-one

(+)-cloprostenol

methyl (8R,9S,11R,12S,15S)-16-(m-chlorophenoxy)-9,11,15-trihydroxy-17,18,19,20-tetranor-5Z,13E-prostadienoate

cloprostenol

Refernces

• 1、 Tolstikov, G. A.,Vostrikov, N. S.,Kuznetsov, O. M.,Singizova, V. Kh.,Khalilov, L. M.,Miftakhov, M. S.. "SYNTHESIS OF THE (+)-ENANTIOMER OF CLOPROSTENOL". . p. 386 - 387. Retrieved 2007/10/02.
• 2、 Schaaf, Thomas K.,Bindra, Jasjit S.,Eggler, James F.,Plattner, Jacob J.,Nelson, A. James,et al.. "N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: Tissue-Selective, Uterine Stimulants". . p. 1353 - 1359. Retrieved 2007/10/02.