6-[5-Oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enylsulfanyl]-hexanoic acid phenyl ester

Base Information

• Chemical Name: 6-[5-Oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enylsulfanyl]-hexanoic acid phenyl ester
• CAS No.: 83009-55-6
• Molecular Formula: C₂₂H₂₈O₅S
• Molecular Weight: 404.527

Synonyms:6-[5-Oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enylsulfanyl]-hexanoic acid phenyl ester

Chemical Property of 6-[5-Oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enylsulfanyl]-hexanoic acid phenyl ester

Chemical Property:

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Technology Process of 6-[5-Oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enylsulfanyl]-hexanoic acid phenyl ester

There total 3 articles about 6-[5-Oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enylsulfanyl]-hexanoic acid phenyl 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: 77.0%

dl-2-(5-carboxypentylthio)-4-(tetrahydropyran-2-yloxy)-2-cyclopentenone (83009-40-9) + phenol (108-95-2,27073-41-2) → 6-[5-Oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enylsulfanyl]-hexanoic acid phenyl ester (83009-55-6)

Guidance literature:

With pyridine; dicyclohexyl-carbodiimide; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1248/cpb.33.2359

Reference yield:

6-mercaptocaproic acid (17689-17-7) → 6-[5-Oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enylsulfanyl]-hexanoic acid phenyl ester (83009-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / triethylamine / methanol

2: 77 percent / dicyclohexylcarbodiimide, pyridine / CH₂Cl₂ / 18 h / Ambient temperature

With pyridine; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1248/cpb.33.2359

Reference yield:

4-(2-tetrahydropyranyloxy)-2,3-epoxycyclopentan-1-one (64079-54-5) → 6-[5-Oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enylsulfanyl]-hexanoic acid phenyl ester (83009-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / triethylamine / methanol

2: 77 percent / dicyclohexylcarbodiimide, pyridine / CH₂Cl₂ / 18 h / Ambient temperature

With pyridine; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1248/cpb.33.2359

upstream raw materials:

dl-2-(5-carboxypentylthio)-4-(tetrahydropyran-2-yloxy)-2-cyclopentenone

phenol

6-mercaptocaproic acid

4-(2-tetrahydropyranyloxy)-2,3-epoxycyclopentan-1-one

Downstream raw materials:

6-[(1S,2R,3S)-2-((E)-(S)-3-Cyclohexyl-3-hydroxy-propenyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-hexanoic acid phenyl ester

6-[(2S,3R)-2-((E)-(S)-3-Cyclohexyl-3-hydroxy-propenyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-hexanoic acid phenyl ester

6-[2-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopentylsulfanyl]-hexanoic acid phenyl ester

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