(3S,3aR,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-8b-methylsulfanylmethoxy-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one

Base Information

• Chemical Name: (3S,3aR,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-8b-methylsulfanylmethoxy-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one
• CAS No.: 145622-44-2
• Molecular Formula: C₂₈H₂₈O₆S
• Molecular Weight: 492.593
• Mol file: 145622-44-2.mol

Synonyms:

Chemical Property of (3S,3aR,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-8b-methylsulfanylmethoxy-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3aR,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-8b-methylsulfanylmethoxy-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one

There total 4 articles about (3S,3aR,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-8b-methylsulfanylmethoxy-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one 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:

(±)-(3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one (117828-45-2,136892-17-6,145679-22-7) → (3S,3aR,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-8b-methylsulfanylmethoxy-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one (145622-44-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 99.5 percent / DIBAL / tetrahydrofuran; hexane / 1) -78 deg C, 30 min, 2) up to r. t., 3 h

2: 1) (COCl)2, DMSO, 2) N(Et)3 / 1) THF, -78 deg C, 30 min, 2) up to r. t.

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane;

Reference yield:

(S)-3-[(R)-4,6-Dimethoxy-2-(4-methoxy-phenyl)-3-oxo-2,3-dihydro-benzofuran-2-yl]-3-phenyl-propionitrile (117828-43-0,117828-44-1) → (3S,3aR,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-8b-methylsulfanylmethoxy-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one (145622-44-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 13.5 percent / SmI₂ / benzene; tetrahydrofuran / 1 h / Ambient temperature; sonication

2: 99.5 percent / DIBAL / tetrahydrofuran; hexane / 1) -78 deg C, 30 min, 2) up to r. t., 3 h

3: 1) (COCl)2, DMSO, 2) N(Et)3 / 1) THF, -78 deg C, 30 min, 2) up to r. t.

With samarium diiodide; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; benzene;

Reference yield:

6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydrocyclopentabenzofuran-1,8b(1H)-diol (136850-46-9,136892-16-5,147059-46-9,147202-06-0) → (±)-(3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one (117828-45-2,136892-17-6,145679-22-7) + (3S,3aR,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-8b-methylsulfanylmethoxy-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one (145622-44-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, -78 deg C, 30 min, 2) up to r. t.;

upstream raw materials:

6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydrocyclopentabenzofuran-1,8b(1H)-diol

dimethyl sulfoxide

(±)-(3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one

(S)-3-[(R)-4,6-Dimethoxy-2-(4-methoxy-phenyl)-3-oxo-2,3-dihydro-benzofuran-2-yl]-3-phenyl-propionitrile

Downstream raw materials:

(±)-(3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one

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

(3S,3aR,8bS)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-1,2,3,3a-tetrahydro-benzo[b]cyclopenta[d]furan-1,8b-diol