(3aS,8bR)-methyl 6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-8b-((trimethylsilyl)oxy)-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate

Base Information

• Chemical Name: (3aS,8bR)-methyl 6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-8b-((trimethylsilyl)oxy)-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate
• CAS No.: 132464-01-8
• Molecular Formula: C₃₁H₃₂O₈Si
• Molecular Weight: 560.676
• Mol file: 132464-01-8.mol

Synonyms:(3aS,8bR)-methyl 6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-8b-((trimethylsilyl)oxy)-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate

Chemical Property of (3aS,8bR)-methyl 6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-8b-((trimethylsilyl)oxy)-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,8bR)-methyl 6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-8b-((trimethylsilyl)oxy)-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate

There total 22 articles about (3aS,8bR)-methyl 6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-8b-((trimethylsilyl)oxy)-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate 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: 96.0%

chloro-trimethyl-silane (75-77-4) + (3aS,8bR)-methyl 8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate (132464-02-9) → (3aS,8bR)-methyl 6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-8b-((trimethylsilyl)oxy)-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate (132464-01-8)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In benzene; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo202366c

Reference yield:

3,5-dimethoxyphenol (500-99-2) → (3aS,8bR)-methyl 6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-8b-((trimethylsilyl)oxy)-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate (132464-01-8)

Guidance literature:

Multi-step reaction with 7 steps

2: 73 percent / DABCO, OsO₄, NMO / tetrahydrofuran; H₂O / Ambient temperature

3: C₅H₅N*SO₃, (C₂H₅)3N / dimethylsulfoxide / Ambient temperature

4: (i-C₃H₇)2NC₂H₅ / benzene / Ambient temperature

5: H₂ / 10percent Pd/C / ethanol / 760 Torr

6: NaH / tetrahydrofuran / Ambient temperature

7: MCPBA, NaHCO₃ / CH₂Cl₂ / -20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; sulfur trioxide pyridine complex; sodium hydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; benzene;

DOI:10.1021/ja00180a081

Reference yield:

3,4-Dimethyl-2-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-[1,4]oxazepane-5,7-dione (65092-79-7,69979-56-2,71830-47-2,71830-48-3) → (3aS,8bR)-methyl 6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-8b-((trimethylsilyl)oxy)-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate (132464-01-8)

Guidance literature:

Multi-step reaction with 8 steps

3: 73 percent / DABCO, OsO₄, NMO / tetrahydrofuran; H₂O / Ambient temperature

4: C₅H₅N*SO₃, (C₂H₅)3N / dimethylsulfoxide / Ambient temperature

5: (i-C₃H₇)2NC₂H₅ / benzene / Ambient temperature

6: H₂ / 10percent Pd/C / ethanol / 760 Torr

7: NaH / tetrahydrofuran / Ambient temperature

8: MCPBA, NaHCO₃ / CH₂Cl₂ / -20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; sulfur trioxide pyridine complex; sodium hydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; benzene;

DOI:10.1021/ja00180a081

upstream raw materials:

3,5-dimethoxyphenol

3,4-Dimethyl-2-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-[1,4]oxazepane-5,7-dione

(2R,3S,3aR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-3,3a-dihydro-benzo[b]cyclopenta[d]furan-2,2-dicarboxylic acid benzyl ester methyl ester

(2S,3S,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3-phenyl-1,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-2,2-dicarboxylic acid benzyl ester methyl ester

Downstream raw materials:

aglafoline

endo rocaglic acid

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

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