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

Base Information

Chemical Name:(1R,2R,3S,3aR,8bS)-methyl 6-amino-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate
CAS No.:1402931-65-0
Molecular Formula:C₂₇H₂₇NO₇
Molecular Weight:477.514
Hs Code.:

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

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

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

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

There total 14 articles about (1R,2R,3S,3aR,8bS)-methyl 6-amino-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[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:

Reference yield: 74.0%

: 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

: 1402931-65-0
(1R,2R,3S,3aR,8bS)-methyl 6-amino-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate

Guidance literature:: (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; With Benzophenone imine; palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100 ℃; for 20h; Inert atmosphere;

With hydroxylamine hydrochloride; sodium acetate; In methanol; at 20 ℃; for 3h; 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

: 1402931-65-0
(1R,2R,3S,3aR,8bS)-methyl 6-amino-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

2.1: Benzophenone imine; palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 20 h / 100 °C / Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

With Benzophenone imine; palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;
DOI:10.1021/jm3011542

Reference yield:

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

: 1402931-65-0
(1R,2R,3S,3aR,8bS)-methyl 6-amino-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate

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: Benzophenone imine; palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 20 h / 100 °C / Inert atmosphere

8.2: 3 h / 20 °C / Inert atmosphere

With Benzophenone imine; sulfuric acid; 5%-palladium/activated carbon; water; hydrogen; palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; acetonitrile; 1.1: |Baker-Venkataraman Rearrangement;
DOI:10.1021/jm3011542