(1R,2R,3S,3aR,8bS)-3a-(4-cyanophenyl)-1,8b-dihydroxy-6,8-dimethoxy-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo-[b]cyclopenta[d]furan-2-carboxamide

Base Information

• Chemical Name: (1R,2R,3S,3aR,8bS)-3a-(4-cyanophenyl)-1,8b-dihydroxy-6,8-dimethoxy-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo-[b]cyclopenta[d]furan-2-carboxamide
• CAS No.: 1139263-21-0
• Molecular Formula: C₂₉H₂₈N₂O₆
• Molecular Weight: 500.551

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

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

Chemical Property:

Purity/Quality:

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

There total 17 articles about (1R,2R,3S,3aR,8bS)-3a-(4-cyanophenyl)-1,8b-dihydroxy-6,8-dimethoxy-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo-[b]cyclopenta[d]furan-2-carboxamide 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:

C27H23NO7 (1139263-24-3) + N,N-dimethylammonium chloride (506-59-2) → (1R,2R,3S,3aR,8bS)-3a-(4-cyanophenyl)-1,8b-dihydroxy-6,8-dimethoxy-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo-[b]cyclopenta[d]furan-2-carboxamide (1139263-21-0)

Guidance literature:

C₂₇H₂₃NO₇; N,N-dimethylammonium chloride; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 12.16h; Inert atmosphere;

DOI:10.1021/jm3011542

Reference yield:

5,7-dihydroxy-2-phenyl-chromen-4-one (480-40-0) → (1R,2R,3S,3aR,8bS)-3a-(4-cyanophenyl)-1,8b-dihydroxy-6,8-dimethoxy-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo-[b]cyclopenta[d]furan-2-carboxamide (1139263-21-0)

Guidance literature:

Multi-step reaction with 17 steps

1.1: potassium carbonate / acetone / 3 h / 60 °C / Inert atmosphere

2.1: acetone / 72 h / 40 °C / Inert atmosphere

3.1: pyridine / water; diethylene glycol / 2 h / 100 °C / Inert atmosphere; Alkaline conditions

4.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

5.2: 6 h / Inert atmosphere; Reflux

6.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.5 h / -70 - -20 °C / Inert atmosphere

8.1: sulfuric acid; acetic acid / 8 h / 75 °C / Inert atmosphere

8.2: 2 h / 20 °C / Inert atmosphere

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

10.1: methanol; dichloromethane; acetonitrile / 3 h / 0 - 5 °C / Inert atmosphere; UV-irradiation

10.2: 1 h / 60 °C / Inert atmosphere

11.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 48 h / Inert atmosphere

12.1: LUX Cellulose-2 / methanol / Inert atmosphere; Resolution of racemate; Supercritical conditions

13.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 20 h / 100 °C / Inert atmosphere

14.1: 5%-palladium/activated carbon; hydrogen / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

15.1: methanol; toluene / 4 h / Inert atmosphere

16.1: lithium hydroxide / methanol; water / 16 h / 45 °C / Inert atmosphere

16.2: Inert atmosphere

17.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

17.2: 12.16 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sulfuric acid; 5%-palladium/activated carbon; water; hydrogen; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; lithium hydroxide; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; acetonitrile; diethylene glycol; 5.1: |Rubottom Oxidation / 5.2: |Rubottom Oxidation / 7.1: |Baker-Venkataraman Rearrangement;

DOI:10.1021/jm3011542

Reference yield:

7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one (110506-85-9) → (1R,2R,3S,3aR,8bS)-3a-(4-cyanophenyl)-1,8b-dihydroxy-6,8-dimethoxy-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo-[b]cyclopenta[d]furan-2-carboxamide (1139263-21-0)

Guidance literature:

Multi-step reaction with 16 steps

1.1: acetone / 72 h / 40 °C / Inert atmosphere

2.1: pyridine / water; diethylene glycol / 2 h / 100 °C / Inert atmosphere; Alkaline conditions

3.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

4.2: 6 h / Inert atmosphere; Reflux

5.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.5 h / -70 - -20 °C / Inert atmosphere

7.1: sulfuric acid; acetic acid / 8 h / 75 °C / Inert atmosphere

7.2: 2 h / 20 °C / Inert atmosphere

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

9.1: methanol; dichloromethane; acetonitrile / 3 h / 0 - 5 °C / Inert atmosphere; UV-irradiation

9.2: 1 h / 60 °C / Inert atmosphere

10.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 48 h / Inert atmosphere

11.1: LUX Cellulose-2 / methanol / Inert atmosphere; Resolution of racemate; Supercritical conditions

12.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 20 h / 100 °C / Inert atmosphere

13.1: 5%-palladium/activated carbon; hydrogen / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

14.1: methanol; toluene / 4 h / Inert atmosphere

15.1: lithium hydroxide / methanol; water / 16 h / 45 °C / Inert atmosphere

15.2: Inert atmosphere

16.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

16.2: 12.16 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sulfuric acid; 5%-palladium/activated carbon; water; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; lithium hydroxide; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; acetonitrile; diethylene glycol; 4.1: |Rubottom Oxidation / 4.2: |Rubottom Oxidation / 6.1: |Baker-Venkataraman Rearrangement;

DOI:10.1021/jm3011542

upstream raw materials:

C₂₇H₂₃NO₇

N,N-dimethylammonium chloride

5,7-dihydroxy-2-phenyl-chromen-4-one

7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one

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