(1R,2R,3S,3aR,8bS)-dimethyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2,6-dicarboxylate

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Chemical Name:(1R,2R,3S,3aR,8bS)-dimethyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2,6-dicarboxylate
CAS No.:1402931-70-7
Molecular Formula:C₂₉H₂₈O₉
Molecular Weight:520.536
Hs Code.:

(1R,2R,3S,3aR,8bS)-dimethyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2,6-dicarboxylate

Synonyms:(1R,2R,3S,3aR,8bS)-dimethyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2,6-dicarboxylate

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Chemical Property of (1R,2R,3S,3aR,8bS)-dimethyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2,6-dicarboxylate

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Technology Process of (1R,2R,3S,3aR,8bS)-dimethyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2,6-dicarboxylate

There total 15 articles about (1R,2R,3S,3aR,8bS)-dimethyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2,6-dicarboxylate 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: 63.0%

: 1402931-69-4
(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-8-methoxy-2-(methoxycarbonyl)-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-6-carboxylic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 1402931-70-7
(1R,2R,3S,3aR,8bS)-dimethyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2,6-dicarboxylate

Guidance literature:: In methanol; toluene; at 22 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jm3011542

Reference yield:

: 960365-65-5
(1R,2R,3S,3aR,8bS)-methyl 1,6,8b-trihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate

: 1402931-70-7
(1R,2R,3S,3aR,8bS)-dimethyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2,6-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.82 h / -10 °C / Inert atmosphere

2: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 2.25 h / 100 °C / Inert atmosphere

3: methanol; toluene / 1 h / 22 °C / Inert atmosphere

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm3011542

Reference yield:

: [2-[4-benzyloxy-2-methoxy-6-(4-methoxybenzoyl)oxyphenyl]-2-oxoethyl] 4-methoxybenzoate

: 1402931-70-7
(1R,2R,3S,3aR,8bS)-dimethyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2,6-dicarboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 - -20 °C / Inert atmosphere

2.1: sulfuric acid; acetic acid / 20 h / 20 °C / Inert atmosphere

3.1: water; sodium hydroxide / ethanol / 1 h / 80 °C / Inert atmosphere

4.1: methanol; dichloromethane; acetonitrile / 10 h / 0 - 5 °C / Inert atmosphere; UV-irradiation

4.2: 1 h / 60 °C / Inert atmosphere

4.3: 48 h / Inert atmosphere

5.1: 5%-palladium/activated carbon; hydrogen / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

6.1: ChiralPak AD-H / ethanol / Inert atmosphere; Supercritical conditions; Resolution of racemate

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.82 h / -10 °C / Inert atmosphere

8.1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 2.25 h / 100 °C / Inert atmosphere

9.1: methanol; toluene / 1 h / 22 °C / Inert atmosphere

With 1,1'-bis-(diphenylphosphino)ferrocene; sulfuric acid; 5%-palladium/activated carbon; water; hydrogen; palladium diacetate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: |Baker-Venkataraman Rearrangement;
DOI:10.1021/jm3011542