61799-74-4

Usage

InChI:InChI=1/C21H34O5/c1-3-4-5-8-15(22)11-12-17-18-13-16(26-20(18)14-19(17)23)9-6-7-10-21(24)25-2/h9,11-12,15,17-20,22-23H,3-8,10,13-14H2,1-2H3/b12-11+,16-9+/t15-,17+,18+,19+,20-/m0/s1

Upstream product

• 75683-18-0 {(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-cyclopent-2-enyl}-acetaldehyde 
• 80282-40-2 7-endo-t-butyldimethylsilyloxy-6-exo-(3-t-butyldimethylsilyloxyoct-1-enyl)-3-exo-<(1R)-2-oxocyclopentyl>-cis-2-oxabicyclo<3.3.0>octane 
• 80282-38-8 threo-β-1-(2-oxocyclopentyl)-2-<4-endo-t-butyldimethylsilyloxy-5-exo-(3-t-butyldimethylsilyloxyoct-1-enyl)cyclopent-2-enyl>ethanol 
• 80282-41-3 7-endo-t-butyldimethylsilyloxy-6-exo-(3-t-butyldimethylsilyloxyoct-1-enyl)-3-exo-<(1R)-6-oxotetrahydropyran-2-yl>-cis-2-oxabicyclo<3.3.0>octane 
• 80282-42-4 (S)-5-{(2S,3aS,4S,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2-yl}-5-hydroxy-pentanoic acid methyl ester 
• 80282-43-5 (S)-5-{(2S,3aS,4S,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2-yl}-5-methanesulfonyloxy-pentanoic acid methyl ester 
• 80282-43-5 (R)-5-{(2R,3aS,4S,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2-yl}-5-methanesulfonyloxy-pentanoic acid methyl ester 
• 80282-42-4 (R)-5-{(2R,3aS,4S,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2-yl}-5-hydroxy-pentanoic acid methyl ester 
• 91788-91-9 (S)-2-{(2S,3aR,4R,5S,6S,6aR)-6-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-4-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2-yl}-cyclopentanone 
• 80282-41-3 (R)-6-{(2R,3aS,4S,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2-yl}-tetrahydro-pyran-2-one 
• 80282-38-8 threo-α-1-(2-oxocyclopentyl)-2-<4-endo-t-butyldimethylsilyloxy-5-exo-(3-t-butyldimethylsilyloxyoct-1-enyl)cyclopent-2-enyl>ethanol 
• 80282-40-2 (R)-2-{(2R,3aS,4S,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2-yl}-cyclopentanone 
• 80282-39-9 7-endo-t-butyldimethylsilyloxy-6-exo-(3-t-butyldimethylsilyloxyoct-1-enyl)-3-exo-<(1R)-2-oxocyclopentyl>-8-exo-iodo-cis-2-oxabicyclo<3.3.0>octane 
• 65844-23-7 (R)-5-[(2R,3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(R)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-5-methanesulfonyloxy-pentanoic acid methyl ester 

Downstream Products

• 35121-78-9 Epoprostenol 
• 63557-55-1 6-keto-PGF_1α methyl ester 
• 75636-73-6 (5E)-5-phenylthio-PGI₂ methyl ester 
• 75636-72-5 7-phenylthio-PGI₂ methyl ester 
• 75636-74-7 5-Benzenesulfinyl-5-[(3aR,5R,6aS)-5-hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-(2E)-ylidene]-pentanoic acid methyl ester 
• 75636-73-6 5-[(3aR,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-(2E)-ylidene]-5-phenylsulfanyl-pentanoic acid methyl ester 
• 75636-72-5 5-[(3aR,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-3-phenylsulfanyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[b]furan-2-yl]-pentanoic acid methyl ester 
• 75636-74-7 (5E)-5-phenethylsulfinyl-PGI₂ methyl ester 

Relevant academic research and scientific papers

Synthesis of (+/-)-Prostaglandin I2 Methyl Ester and its 15-Epimer from 2-(Cyclopent-2-enyl)-1-(2-oxocyclopentyl)ethanol Derivatives

The threo-2-(cyclopent-2-enyl)-1-(2-oxocyclopentyl)ethanol derivatives (2) and (3) have been converted into (+/-)-prostaglandin I2 methyl ester and its 15-epimer.The route involved halogenoetherification, hydrodehalogenation, Baeyer-Villiger oxidation, and methanolysis, to give the 5-hydroxyprostaglandin I1 derivatives (17) and (18).These hydroxy esters were mesylated, the 11- and 15-hydroxy groups were deprotected, and the resulting 15-epimeric alcohols were separated.The final elimination, accomplished by means of neat 1,8-diazabicycloundec-7-ene, gave the required Δ5-olefin with a high degree of regioselectivity, and was stereospecifically trans, giving the required Z-configuration (25).

A SHORT WAY TO PROSTACYCLIN

A facile, stereospecific preparation of prostacyclin has been accomplished starting from a 5,6-dehydroprostaglandin F2α derivative.

Total Synthesis of (+/-)-Prostaglandin I2 Methyl Ester and (+/-)-15-epi-Prostaglandin I2 Methyl Ester

Prostacyclin (prostaglandin I2) methyl ester has been prepared; the key step was an aldol reaction between a cyclopentanone enolate and the cyclopentenylacetaldehyde derivative (4).