5-[(3aR,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-(2Z)-ylidene]-pentanoic acid methyl ester

Base Information

• Chemical Name: 5-[(3aR,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-(2Z)-ylidene]-pentanoic acid methyl ester
• CAS No.: 63557-59-5
• Molecular Formula: C₂₁H₃₄O₅
• Molecular Weight: 366.498
• Mol file: 63557-59-5.mol

Synonyms:

Chemical Property of 5-[(3aR,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-(2Z)-ylidene]-pentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(3aR,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-(2Z)-ylidene]-pentanoic acid methyl ester

There total 35 articles about 5-[(3aR,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-(2Z)-ylidene]-pentanoic acid methyl ester 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: 68.0%

(+/-)-(5R)-mesyloxy-(6S)-prostaglandin I1 methyl ester (65844-23-7,80300-73-8,80300-74-9,91840-61-8,91840-62-9,91840-63-0) → (+/-)-prostaglandin I2 methyl ester (61799-74-4,63557-59-5,64812-61-9,70773-80-7,75419-26-0,75419-27-1,75419-28-2,75420-33-6,80300-75-0,80300-76-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene;

DOI:10.1039/c39810000922

Reference yield: 56.0%

(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 (65844-23-7,80300-73-8,80300-74-9,91840-61-8,91840-62-9,91840-63-0) → (+/-)-15-epi-prostaglandin I2 methyl ester (61799-74-4,63557-59-5,64812-61-9,70773-80-7,75419-26-0,75419-27-1,75419-28-2,75420-33-6,80300-75-0,80300-76-1) + (E)-5-[(2S,3aS,4S,5S,6aR)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-pent-4-enoic acid methyl ester (64861-48-9,67529-24-2,67529-25-3,91840-64-1,91840-65-2,91840-66-3,91840-67-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 60 ℃; for 20h;

DOI:10.1039/P19840000675

Reference yield: 56.0%

(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 (65844-23-7,80300-73-8,80300-74-9,91840-61-8,91840-62-9,91840-63-0) → (+/-)-15-epi-prostaglandin I2 methyl ester (61799-74-4,63557-59-5,64812-61-9,70773-80-7,75419-26-0,75419-27-1,75419-28-2,75420-33-6,80300-75-0,80300-76-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene;

DOI:10.1039/c39810000922

upstream raw materials:

(+/-)-(5S)-mesyloxy-(6R)-prostaglandin I₁ methyl ester

(+/-)-(5R)-mesyloxy-(6S)-prostaglandin I₁ methyl ester

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

{(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-cyclopent-2-enyl}-acetaldehyde

Downstream raw materials:

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

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

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