(3aS,8bS)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3a,8b-dihydro-1H-benzo[b]cyclopenta[d]furan-2-carbothioic acid S-methyl ester

Base Information

• Chemical Name: (3aS,8bS)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3a,8b-dihydro-1H-benzo[b]cyclopenta[d]furan-2-carbothioic acid S-methyl ester
• CAS No.: 117828-40-7
• Molecular Formula: C₂₂H₂₀O₇S
• Molecular Weight: 428.463
• Mol file: 117828-40-7.mol

Synonyms:(3aS,8bS)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3a,8b-dihydro-1H-benzo[b]cyclopenta[d]furan-2-carbothioic acid S-methyl ester

Chemical Property of (3aS,8bS)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3a,8b-dihydro-1H-benzo[b]cyclopenta[d]furan-2-carbothioic acid S-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,8bS)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3a,8b-dihydro-1H-benzo[b]cyclopenta[d]furan-2-carbothioic acid S-methyl ester

There total 2 articles about (3aS,8bS)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3a,8b-dihydro-1H-benzo[b]cyclopenta[d]furan-2-carbothioic acid S-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: 56.0%

(3aS,8bS)-2-(Bis-methylsulfanyl-methylene)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one (117828-39-4) → (3aS,8bS)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3a,8b-dihydro-1H-benzo[b]cyclopenta[d]furan-2-carbothioic acid S-methyl ester (117828-40-7)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In water; acetonitrile; for 48h; Heating;

DOI:10.1021/jo00262a022

Reference yield:

(3aS,8bS)-2-(Bis-methylsulfanyl-methylene)-6,8-dimethoxy-3a-(4-methoxy-phenyl)-8b-trimethylsilanyloxy-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one (117828-38-3) → (3aS,8bS)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3a,8b-dihydro-1H-benzo[b]cyclopenta[d]furan-2-carbothioic acid S-methyl ester (117828-40-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / tetra-n-butylammonium fluoride

2: 56 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / acetonitrile; H₂O / 48 h / Heating

With tetrabutyl ammonium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In water; acetonitrile;

DOI:10.1021/jo00262a022

Reference yield:

(3aS,8bS)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3a,8b-dihydro-1H-benzo[b]cyclopenta[d]furan-2-carbothioic acid S-methyl ester (117828-40-7) → (3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylic acid dimethylamide (117828-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) CuBr-Me₂S / 1.) diethyl ether, 0 deg C, 25 min, 2a.) -78 deg C, 1 h, 2b.) from -78 deg C to RT, 3 h

2: 92 percent / tetrahydrofuran / 48 h / 75 °C

With 1.) CuBr-Me₂S; In tetrahydrofuran;

DOI:10.1021/jo00262a022

upstream raw materials:

(3aS,8bS)-2-(Bis-methylsulfanyl-methylene)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one

(3aS,8bS)-2-(Bis-methylsulfanyl-methylene)-6,8-dimethoxy-3a-(4-methoxy-phenyl)-8b-trimethylsilanyloxy-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one

Downstream raw materials:

(3aR,8bS)-1,8b-Dihydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-3a,8b-dihydro-3H-benzo[b]cyclopenta[d]furan-2-carbothioic acid S-methyl ester

(3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylic acid dimethylamide

(3aR,8bS)-1,8b-Dihydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylic acid dimethylamide