(1S,3S,3aR,7aS)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-1-ethenyl-2,3,3a,4,7,7a-hexahydro-7-methylene-1H-inden-4-ol

Base Information

• Chemical Name: (1S,3S,3aR,7aS)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-1-ethenyl-2,3,3a,4,7,7a-hexahydro-7-methylene-1H-inden-4-ol
• CAS No.: 944282-81-9
• Molecular Formula: C₂₆H₃₈O₃Si
• Molecular Weight: 426.671
• Mol file: 944282-81-9.mol

Synonyms:(1S,3S,3aR,7aS)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-1-ethenyl-2,3,3a,4,7,7a-hexahydro-7-methylene-1H-inden-4-ol

Chemical Property of (1S,3S,3aR,7aS)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-1-ethenyl-2,3,3a,4,7,7a-hexahydro-7-methylene-1H-inden-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,3aR,7aS)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-1-ethenyl-2,3,3a,4,7,7a-hexahydro-7-methylene-1H-inden-4-ol

There total 11 articles about (1S,3S,3aR,7aS)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-1-ethenyl-2,3,3a,4,7,7a-hexahydro-7-methylene-1H-inden-4-ol 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: 93.0%

(1R,2S,3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-α,3-diethenyl-2-(1-methylene-2-propen-1-yl)cyclopentanemethanol (944282-80-8) → (1S,3S,3aR,7aS)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-1-ethenyl-2,3,3a,4,7,7a-hexahydro-7-methylene-1H-inden-4-ol (944282-81-9)

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1002/anie.200700517

Reference yield:

C21H34O4Si (944282-73-9) → (1S,3S,3aR,7aS)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-1-ethenyl-2,3,3a,4,7,7a-hexahydro-7-methylene-1H-inden-4-ol (944282-81-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: pyridine / tetrahydrofuran / 1.5 h / 0 - 20 °C

2.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3.1: 82 percent / SmI₂ / methanol; tetrahydrofuran / 5 h / 0 °C

4.1: potassium 1,1,1,3,3,3-hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

4.2: 92 percent / tetrahydrofuran / 2 h

5.1: 77 percent / Ph₃P; Et₃N / Pd(OAc)2 / dimethylformamide / 24 h

6.1: diisobutylaluminum hydride / CH₂Cl₂ / 1 h / -78 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 0.75 h

8.1: Mg; ZnCl₂ / tetrahydrofuran; toluene / 1 h / Heating

8.2: CuBr*SMe₂; Me₃SiCl / hexamethylphosphoric acid triamide; tetrahydrofuran; toluene / -78 °C

8.3: 60 percent / CF₃COOH / hexamethylphosphoric acid triamide; tetrahydrofuran; toluene / 0 °C

9.1: 69 percent / tetrahydrofuran / 0.75 h / 0 °C

10.1: 93 percent / bis(tricyclohexylphosphine) benzylidene Ru(IV) dichloride / CH₂Cl₂ / 24 h / 20 °C

With pyridine; samarium diiodide; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; triethylamine; triphenylphosphine; zinc(II) chloride; palladium diacetate; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/anie.200700517

Reference yield:

C26H42O5Si → (1S,3S,3aR,7aS)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-1-ethenyl-2,3,3a,4,7,7a-hexahydro-7-methylene-1H-inden-4-ol (944282-81-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

2.1: 82 percent / SmI₂ / methanol; tetrahydrofuran / 5 h / 0 °C

3.1: potassium 1,1,1,3,3,3-hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

3.2: 92 percent / tetrahydrofuran / 2 h

4.1: 77 percent / Ph₃P; Et₃N / Pd(OAc)2 / dimethylformamide / 24 h

5.1: diisobutylaluminum hydride / CH₂Cl₂ / 1 h / -78 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 0.75 h

7.1: Mg; ZnCl₂ / tetrahydrofuran; toluene / 1 h / Heating

7.2: CuBr*SMe₂; Me₃SiCl / hexamethylphosphoric acid triamide; tetrahydrofuran; toluene / -78 °C

7.3: 60 percent / CF₃COOH / hexamethylphosphoric acid triamide; tetrahydrofuran; toluene / 0 °C

8.1: 69 percent / tetrahydrofuran / 0.75 h / 0 °C

9.1: 93 percent / bis(tricyclohexylphosphine) benzylidene Ru(IV) dichloride / CH₂Cl₂ / 24 h / 20 °C

With samarium diiodide; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; triethylamine; triphenylphosphine; zinc(II) chloride; palladium diacetate; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/anie.200700517

upstream raw materials:

(1R,2S,3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-α,3-diethenyl-2-(1-methylene-2-propen-1-yl)cyclopentanemethanol

C₂₁H₃₄O₄Si

2,2-dimethylpropanoic acid [(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-oxobicyclo[3.1.0]hexan-6-yl]methyl ester

(2S,4R)-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-4-ethenylcyclopentanone

Downstream raw materials:

(1S,3S,3aR,7aS)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-1-ethenyl-2,3,3a,4,7,7a-hexahydro-7-methylene-1H-inden-4-one