(3aS,5aS,9aS,9bR)-3a-allyl-6,6,9a-trimethyl-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

Base Information

• Chemical Name: (3aS,5aS,9aS,9bR)-3a-allyl-6,6,9a-trimethyl-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole
• CAS No.: 1415010-31-9
• Molecular Formula: C₂₇H₄₂N₂O₅SSi
• Molecular Weight: 534.792

Synonyms:(3aS,5aS,9aS,9bR)-3a-allyl-6,6,9a-trimethyl-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

Chemical Property of (3aS,5aS,9aS,9bR)-3a-allyl-6,6,9a-trimethyl-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (3aS,5aS,9aS,9bR)-3a-allyl-6,6,9a-trimethyl-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

There total 15 articles about (3aS,5aS,9aS,9bR)-3a-allyl-6,6,9a-trimethyl-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole 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: 92.0%

2-((1'R,2S,3S,4a'S,8a'S)-5',5',8a'-trimethyl-1-(2-nitrobenzenesulfonyl)-1'-trimetylsilyloxy-3-vinyloctahydro-1'H-spiro[aziridine-2,2'-naphthalen]-1'-yl)ethyl 2-nitrobenzenesulfonate → (3aS,5aS,9aS,9bR)-3a-allyl-6,6,9a-trimethyl-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole (1415010-31-9)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 20.1667h; Inert atmosphere;

DOI:10.1021/ol302880x

Reference yield:

(-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one (60134-39-6) → (3aS,5aS,9aS,9bR)-3a-allyl-6,6,9a-trimethyl-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole (1415010-31-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid; water / dichloromethane / 0.33 h / 0 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

4.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C

5.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

5.2: 0.08 h / Inert atmosphere

6.1: tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C

8.1: cyclohexane; borane-THF / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

8.2: 0.5 h / 20 °C / Inert atmosphere

9.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 - 20 °C / Inert atmosphere

10.1: hydrazine / chloroform / 0.33 h / 20 °C

11.1: acetic acid / ethanol / 12 h / Reflux

12.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

12.2: 0.08 h / 0 °C

13.1: tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

14.1: pyridine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

14.2: 24 h / 20 °C / Inert atmosphere

15.1: triphenylphosphine; acetic acid; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triethylamine / tetrahydrofuran / 20.17 h / 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; borane-THF; cyclohexane; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; hydrazine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform; toluene;

DOI:10.1021/ol302880x

Reference yield:

C16H32OSi → (3aS,5aS,9aS,9bR)-3a-allyl-6,6,9a-trimethyl-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole (1415010-31-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 3-chloro-benzenecarboperoxoic acid; water / dichloromethane / 0.33 h / 0 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

3.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C

4.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

4.2: 0.08 h / Inert atmosphere

5.1: tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C

7.1: cyclohexane; borane-THF / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

7.2: 0.5 h / 20 °C / Inert atmosphere

8.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 - 20 °C / Inert atmosphere

9.1: hydrazine / chloroform / 0.33 h / 20 °C

10.1: acetic acid / ethanol / 12 h / Reflux

11.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

11.2: 0.08 h / 0 °C

12.1: tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

13.1: pyridine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

13.2: 24 h / 20 °C / Inert atmosphere

14.1: triphenylphosphine; acetic acid; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triethylamine / tetrahydrofuran / 20.17 h / 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; borane-THF; cyclohexane; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; hydrazine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform; toluene;

DOI:10.1021/ol302880x

upstream raw materials:

(-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one

(2R,4aS,8aS)-(-)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2α-hydroxy-5,5,8aβ-trimethyl-1-oxonaphthalene

(1R,4aS,8aS)-1-hydroxy-5,5,8a-trimethyl-1-vinyloctahydronaphthalen-1(2H)-one

(1R,4aS,8aS)-1-hydroxy-1-(2-hydroxyethyl)-5,5,8a-trimethyloctahydronaphthalen-1(2H)-one

Downstream raw materials:

2-(3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3-[(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indol-3a-yl]acetaldehyde

(3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3a-(3-methylbut-2-enyl)-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

(3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3a-(3-methylbut-2-enyl)-3-(2-nitrobenzenesulfonyl)-9b-hydroxyperhydro-1H-benzo[e]indole

(3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3a-(3-methylbut-2-enyl)-3-(2-nitrobenzenesulfonyl)-3,3a,4,5,5a,6,7,8,9,9a-decahydro-2H-benzo[e]indole

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