(3aS,6aS)-5-Methyl-4-phenylsulfanyl-3a,6a-dihydro-3H-cyclopenta[c]furan-1,6-dione

Base Information

• Chemical Name: (3aS,6aS)-5-Methyl-4-phenylsulfanyl-3a,6a-dihydro-3H-cyclopenta[c]furan-1,6-dione
• CAS No.: 83036-37-7
• Molecular Formula: C₁₄H₁₂O₃S
• Molecular Weight: 260.313
• Mol file: 83036-37-7.mol

Synonyms:(3aS,6aS)-5-Methyl-4-phenylsulfanyl-3a,6a-dihydro-3H-cyclopenta[c]furan-1,6-dione

Chemical Property of (3aS,6aS)-5-Methyl-4-phenylsulfanyl-3a,6a-dihydro-3H-cyclopenta[c]furan-1,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,6aS)-5-Methyl-4-phenylsulfanyl-3a,6a-dihydro-3H-cyclopenta[c]furan-1,6-dione

There total 2 articles about (3aS,6aS)-5-Methyl-4-phenylsulfanyl-3a,6a-dihydro-3H-cyclopenta[c]furan-1,6-dione 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: 90.0%

2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methyl-5-oxo-3-phenylsulfanyl-cyclopent-3-enecarboxylic acid methyl ester (83036-33-3) → (3aS,6aS)-5-Methyl-4-phenylsulfanyl-3a,6a-dihydro-3H-cyclopenta[c]furan-1,6-dione (83036-37-7)

Guidance literature:

With hydrogen bromide; In acetic acid; for 3h; Ambient temperature;

DOI:10.1246/cl.1982.815

Reference yield:

methyl (E)-3-lithio-2-methyl-3-phenylthioprop-2-enoate (71847-75-1,79562-16-6) → (3aS,6aS)-5-Methyl-4-phenylsulfanyl-3a,6a-dihydro-3H-cyclopenta[c]furan-1,6-dione (83036-37-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / 1.) -50 deg C to 0 deg C, 2 h., 2.) 0 deg C, 15 h.

2: 90 percent / concd. HBr / acetic acid / 3 h / Ambient temperature

With hydrogen bromide; In acetic acid;

DOI:10.1246/cl.1982.815

Reference yield: 65.0%

methyllithium (917-54-4) + (3aS,6aS)-5-Methyl-4-phenylsulfanyl-3a,6a-dihydro-3H-cyclopenta[c]furan-1,6-dione (83036-37-7) → (3aS,6S,6aS)-6-Hydroxy-5,6-dimethyl-4-phenylsulfanyl-3,3a,6,6a-tetrahydro-cyclopenta[c]furan-1-one (83036-38-8)

Guidance literature:

at -78 - -40 ℃; for 2h;

DOI:10.1246/cl.1982.815

upstream raw materials:

2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methyl-5-oxo-3-phenylsulfanyl-cyclopent-3-enecarboxylic acid methyl ester

methyl (E)-3-lithio-2-methyl-3-phenylthioprop-2-enoate

Downstream raw materials:

(3aS,6S,6aS)-6-Hydroxy-5,6-dimethyl-4-phenylsulfanyl-3,3a,6,6a-tetrahydro-cyclopenta[c]furan-1-one