2-((3S,3aR,5R,6aS)-3,3a-Dimethyl-4-methylene-2-oxo-3-phenylsulfanyl-hexahydro-cyclopenta[b]furan-5-yloxy)-3-hydroxy-4-methyl-pent-4-enoic acid ethyl ester

Base Information

• Chemical Name: 2-((3S,3aR,5R,6aS)-3,3a-Dimethyl-4-methylene-2-oxo-3-phenylsulfanyl-hexahydro-cyclopenta[b]furan-5-yloxy)-3-hydroxy-4-methyl-pent-4-enoic acid ethyl ester
• CAS No.: 117182-25-9
• Molecular Formula: C₂₄H₃₀O₆S
• Molecular Weight: 446.565

Synonyms:

Chemical Property of 2-((3S,3aR,5R,6aS)-3,3a-Dimethyl-4-methylene-2-oxo-3-phenylsulfanyl-hexahydro-cyclopenta[b]furan-5-yloxy)-3-hydroxy-4-methyl-pent-4-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((3S,3aR,5R,6aS)-3,3a-Dimethyl-4-methylene-2-oxo-3-phenylsulfanyl-hexahydro-cyclopenta[b]furan-5-yloxy)-3-hydroxy-4-methyl-pent-4-enoic acid ethyl ester

There total 9 articles about 2-((3S,3aR,5R,6aS)-3,3a-Dimethyl-4-methylene-2-oxo-3-phenylsulfanyl-hexahydro-cyclopenta[b]furan-5-yloxy)-3-hydroxy-4-methyl-pent-4-enoic acid ethyl 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:

2-Methylcyclopentane-1,3-dione (765-69-5) → 2-((3S,3aR,5R,6aS)-3,3a-Dimethyl-4-methylene-2-oxo-3-phenylsulfanyl-hexahydro-cyclopenta[b]furan-5-yloxy)-3-hydroxy-4-methyl-pent-4-enoic acid ethyl ester (117144-93-1,117182-25-9)

Guidance literature:

Multi-step reaction with 10 steps

2: 93 percent / t-BuOK, t-BuOH / tetrahydrofuran / 20 °C

3: 75 percent / SeO₂, t-BuOOH / 1,2-dichloro-ethane / 6 h / Heating

4: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

5: 1.) lithium diisopropylamide (LDA), 2.) hexamethylphosphoric triamide (HMPA) / 1.) THF, -78 deg C, 0.75 h, 2.) from -78 deg C to 20 deg C, 2 h

6: 90 percent / (n-Bu)4NF / tetrahydrofuran / 10 h / 20 °C

7: 91 percent / Ph₃P, diethyl azodicarboxylate (DEAD) / tetrahydrofuran / 12 h / 20 °C

8: 95 percent / K₂CO₃ / methanol; H₂O / 10 h / 20 °C

9: 1.) TlOEt / 1.) benzene, 20 deg C, 10 h, 2.) CH₃CN, 20 deg C, 3 h

10: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 0.25 h, 2.) -78 deg C, 1 h

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; selenium(IV) oxide; potassium tert-butylate; tetrabutyl ammonium fluoride; thallium (I) ethoxide; potassium carbonate; triphenylphosphine; tert-butyl alcohol; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1021/jo00258a049

Reference yield:

(3S,3aS,6aR)-3,3a-Dimethyl-4-methylene-hexahydro-cyclopenta[b]furan-2-one → 2-((3S,3aR,5R,6aS)-3,3a-Dimethyl-4-methylene-2-oxo-3-phenylsulfanyl-hexahydro-cyclopenta[b]furan-5-yloxy)-3-hydroxy-4-methyl-pent-4-enoic acid ethyl ester (117144-93-1,117182-25-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 75 percent / SeO₂, t-BuOOH / 1,2-dichloro-ethane / 6 h / Heating

2: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

3: 1.) lithium diisopropylamide (LDA), 2.) hexamethylphosphoric triamide (HMPA) / 1.) THF, -78 deg C, 0.75 h, 2.) from -78 deg C to 20 deg C, 2 h

4: 90 percent / (n-Bu)4NF / tetrahydrofuran / 10 h / 20 °C

5: 91 percent / Ph₃P, diethyl azodicarboxylate (DEAD) / tetrahydrofuran / 12 h / 20 °C

6: 95 percent / K₂CO₃ / methanol; H₂O / 10 h / 20 °C

7: 1.) TlOEt / 1.) benzene, 20 deg C, 10 h, 2.) CH₃CN, 20 deg C, 3 h

8: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 0.25 h, 2.) -78 deg C, 1 h

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; selenium(IV) oxide; tetrabutyl ammonium fluoride; thallium (I) ethoxide; potassium carbonate; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1021/jo00258a049

Reference yield:

(3aR,6aR)-3,3a-Dimethyl-tetrahydro-cyclopenta[b]furan-2,4-dione (117144-90-8) → 2-((3S,3aR,5R,6aS)-3,3a-Dimethyl-4-methylene-2-oxo-3-phenylsulfanyl-hexahydro-cyclopenta[b]furan-5-yloxy)-3-hydroxy-4-methyl-pent-4-enoic acid ethyl ester (117144-93-1,117182-25-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / t-BuOK, t-BuOH / tetrahydrofuran / 20 °C

2: 75 percent / SeO₂, t-BuOOH / 1,2-dichloro-ethane / 6 h / Heating

3: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

4: 1.) lithium diisopropylamide (LDA), 2.) hexamethylphosphoric triamide (HMPA) / 1.) THF, -78 deg C, 0.75 h, 2.) from -78 deg C to 20 deg C, 2 h

5: 90 percent / (n-Bu)4NF / tetrahydrofuran / 10 h / 20 °C

6: 91 percent / Ph₃P, diethyl azodicarboxylate (DEAD) / tetrahydrofuran / 12 h / 20 °C

7: 95 percent / K₂CO₃ / methanol; H₂O / 10 h / 20 °C

8: 1.) TlOEt / 1.) benzene, 20 deg C, 10 h, 2.) CH₃CN, 20 deg C, 3 h

9: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 0.25 h, 2.) -78 deg C, 1 h

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; selenium(IV) oxide; potassium tert-butylate; tetrabutyl ammonium fluoride; thallium (I) ethoxide; potassium carbonate; triphenylphosphine; tert-butyl alcohol; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1021/jo00258a049

upstream raw materials:

2-Methylcyclopentane-1,3-dione

(3aR,6aR)-3,3a-Dimethyl-tetrahydro-cyclopenta[b]furan-2,4-dione

(3S,3aS,5R,6aR)-5-Hydroxy-3,3a-dimethyl-4-methylene-hexahydro-cyclopenta[b]furan-2-one

(3S,3aR,5R,6aS)-5-Hydroxy-3,3a-dimethyl-4-methylene-3-phenylsulfanyl-hexahydro-cyclopenta[b]furan-2-one

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