(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

Base Information

Chemical Name:(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
CAS No.:1402931-69-4
Molecular Formula:C₂₈H₂₆O₉
Molecular Weight:506.509
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 14 articles about (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 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: 74.0%

: 201230-82-2
carbon monoxide

: 1402931-62-7
(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate

: 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

Guidance literature:: With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 2.25h; 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

: 1402931-69-4
(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

Guidance literature:: Multi-step reaction with 2 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

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

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 8 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

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; acetonitrile; 1.1: |Baker-Venkataraman Rearrangement;
DOI:10.1021/jm3011542