(S)-3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-but-1-enyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-2-trimethylsilanylmethyl-cyclohex-2-enone

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Chemical Name:(S)-3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-but-1-enyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-2-trimethylsilanylmethyl-cyclohex-2-enone
CAS No.:178559-24-5
Molecular Formula:C₃₅H₇₂O₄Si₄
Molecular Weight:669.296
Hs Code.:

(S)-3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-but-1-enyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-2-trimethylsilanylmethyl-cyclohex-2-enone

Synonyms:(S)-3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-but-1-enyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-2-trimethylsilanylmethyl-cyclohex-2-enone

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Chemical Property of (S)-3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-but-1-enyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-2-trimethylsilanylmethyl-cyclohex-2-enone

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Technology Process of (S)-3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-but-1-enyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-2-trimethylsilanylmethyl-cyclohex-2-enone

There total 13 articles about (S)-3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-but-1-enyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-2-trimethylsilanylmethyl-cyclohex-2-enone 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:

: (S)-3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-but-1-enyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-1-triethylsilanyloxy-2-trimethylsilanylmethyl-cyclohexene

: 178559-24-5
(S)-3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-but-1-enyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-2-trimethylsilanylmethyl-cyclohex-2-enone

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; Ambient temperature;
DOI:10.1021/ja960642f

Reference yield:

: 178559-16-5
(S)-4-Dimethylcarbamoyl-2-hydroxymethyl-2-methyl-butyric acid methyl ester

: 178559-24-5
(S)-3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-but-1-enyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-2-trimethylsilanylmethyl-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 10 steps

1: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

2: tetrahydrofuran / 2 h / -78 °C

3: tetrahydrofuran / 8 h / Ambient temperature

4: 1.) NaH, 2.) π-allylpalladium chloride dimer, Ph3P / 1.) THF, RT, 10 min, 2.) THF, 70 deg C, overnight

5: 90 percent / NaBH₄ / ethanol; tetrahydrofuran / 48 h / 80 °C

6: 94 percent / imidazole / dimethylformamide / 70 °C

7: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, -78 deg C, 5 min, 2.) THF, from -78 deg C to -20 deg C

8: 83 percent / Pd₂(dibenzylideneacetone)3*CHCl₃, dibenzylideneacetone, HCO₂H / toluene / 35 h / Ambient temperature

9: <(CH₂=CHSi(CH₃)2>2Pt / toluene / 70 °C

10: 4.1 mg / DDQ / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; n-butyllithium; formic acid; oxalyl dichloride; bis(η3-allyl-μ-chloropalladium(II)); <(CH2=CHSi(CH3)2>2Pt; boron trifluoride diethyl etherate; sodium hydride; dimethyl sulfoxide; 1,5-diphenyl-1,4-pentadiene-3-one; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja960642f

Reference yield:

: (S)-2-(2-Dimethylcarbamoyl-ethyl)-3-hydroxy-2-methyl-pent-4-enoic acid methyl ester

: 178559-24-5
(S)-3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-but-1-enyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-2-trimethylsilanylmethyl-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 8 steps

1: tetrahydrofuran / 8 h / Ambient temperature

2: 1.) NaH, 2.) π-allylpalladium chloride dimer, Ph3P / 1.) THF, RT, 10 min, 2.) THF, 70 deg C, overnight

3: 90 percent / NaBH₄ / ethanol; tetrahydrofuran / 48 h / 80 °C

4: 94 percent / imidazole / dimethylformamide / 70 °C

5: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, -78 deg C, 5 min, 2.) THF, from -78 deg C to -20 deg C

6: 83 percent / Pd₂(dibenzylideneacetone)3*CHCl₃, dibenzylideneacetone, HCO₂H / toluene / 35 h / Ambient temperature

7: <(CH₂=CHSi(CH₃)2>2Pt / toluene / 70 °C

8: 4.1 mg / DDQ / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; n-butyllithium; formic acid; bis(η3-allyl-μ-chloropalladium(II)); <(CH2=CHSi(CH3)2>2Pt; boron trifluoride diethyl etherate; sodium hydride; 1,5-diphenyl-1,4-pentadiene-3-one; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja960642f