(2R)-2-[(1R,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

Base Information

• Chemical Name: (2R)-2-[(1R,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile
• CAS No.: 936368-29-5
• Molecular Formula: C₂₉H₄₅NO₃Si
• Molecular Weight: 483.767

Synonyms:(2R)-2-[(1R,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

Chemical Property of (2R)-2-[(1R,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2R)-2-[(1R,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

There total 10 articles about (2R)-2-[(1R,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile 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: 87.0%

[(1S,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]acetonitrile (936368-36-4) + methyl iodide (74-88-4) → (2R)-2-[(1R,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile (936368-29-5) + (2S)-2-[(1R,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

Guidance literature:

[(1S,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]acetonitrile; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -80 ℃; for 1h;

methyl iodide; In tetrahydrofuran; hexane; at -80 ℃; for 0.5h; Further stages.;

DOI:10.1021/ol070049a

Reference yield:

ethyl (2E,4S,6R,8E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6,9-dimethyl-10-oxodeca-2,8-dienoate (936368-33-1) → (2R)-2-[(1R,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile (936368-29-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

1.2: tetrahydrofuran / -80 - 0 °C

1.3: CHCl₃ / 2 h / 60 °C

2.1: 1.610 g / diisobutylaluminium hydride / CH₂Cl₂ / -20 - 23 °C

3.1: 94 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

4.1: 98 percent / dimethylsulfoxide / 72 h / 50 °C

5.1: lithium diisopropylamide / hexane; tetrahydrofuran / 1 h / -80 °C

5.2: 87 percent / hexane; tetrahydrofuran / 0.5 h / -80 °C

With potassium tert-butylate; diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ol070049a

Reference yield:

ethyl (1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate (936368-35-3) → (2R)-2-[(1R,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile (936368-29-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1.610 g / diisobutylaluminium hydride / CH₂Cl₂ / -20 - 23 °C

2.1: 94 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

3.1: 98 percent / dimethylsulfoxide / 72 h / 50 °C

4.1: lithium diisopropylamide / hexane; tetrahydrofuran / 1 h / -80 °C

4.2: 87 percent / hexane; tetrahydrofuran / 0.5 h / -80 °C

With diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ol070049a

upstream raw materials:

[(1S,2R,4aS,6R,8S,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]acetonitrile

methyl iodide

ethyl (2E,4S,6R,8E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6,9-dimethyl-10-oxodeca-2,8-dienoate

ethyl (1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Downstream raw materials:

(2R)-2-[(1R,2R,4aS,6R,8S,8aR)-2-(3,5-dimethoxyphenyl)-8-hydroxy-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

(2R)-2-[(1R,2R,4aS,6R,8aR)-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

(2R)-2-[(3'R,4a'S,7'R,8'R,8a'R)-7'-(3,5-dimethoxyphenyl)-3',5'-dimethyl-3',4',4a',7',8',8a'-hexahydro-2'H-spiro[1,3-dioxolane-2,1'-naphthalen]-8'-yl]propanenitrile

C₂₅H₃₇NO₄

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