(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

Base Information

Chemical Name:(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
CAS No.:944282-80-8
Molecular Formula:C₂₈H₄₂O₃Si
Molecular Weight:454.725
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 11 articles about (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 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: 69.0%

: C₂₆H₃₈O₃Si

: 1826-67-1
vinyl magnesium bromide

: 944282-80-8
(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

Guidance literature:: In tetrahydrofuran; at 0 ℃; for 0.75h;
DOI:10.1002/anie.200700517

Reference yield: 69.0%

: (3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-2-(1-methylene-2-propen-1-yl)cyclopentenecarboxaldehyde

: 1826-67-1
vinyl magnesium bromide

: 944282-80-8
(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

Guidance literature:: In tetrahydrofuran; at 0 ℃; for 0.75h;
DOI:10.1021/jo702635t

Reference yield:

: 944282-73-9
C₂₁H₃₄O₄Si

: 944282-80-8
(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

Guidance literature:: Multi-step reaction with 9 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

With pyridine; samarium diiodide; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; triethylamine; triphenylphosphine; zinc(II) chloride; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/anie.200700517