Technology Process of (1R,2R,3S,3aR,8bS)-methyl 6-carbamoyl-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-2-carboxylate
There total 15 articles about (1R,2R,3S,3aR,8bS)-methyl 6-carbamoyl-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-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:
- Guidance literature:
-
With
ammonium acetate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
at 22 ℃;
Inert atmosphere;
DOI:10.1021/jm3011542
- 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: ammonium acetate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 22 °C / Inert atmosphere
With
1,1'-bis-(diphenylphosphino)ferrocene; ammonium acetate; palladium diacetate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine;
In
dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm3011542
- 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: ammonium acetate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 22 °C / Inert atmosphere
With
1,1'-bis-(diphenylphosphino)ferrocene; sulfuric acid; 5%-palladium/activated carbon; ammonium acetate; water; hydrogen; palladium diacetate; potassium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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
![(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](/Databaselist/images/loading.webp)
