[(2E,6Z)-(4S,5S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-2,6-dienyloxymethyl]-benzene

Base Information

Chemical Name:[(2E,6Z)-(4S,5S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-2,6-dienyloxymethyl]-benzene
CAS No.:321921-92-0
Molecular Formula:C₂₈H₅₀O₃Si₂
Molecular Weight:490.874
Hs Code.:

Synonyms:[(2E,6Z)-(4S,5S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-2,6-dienyloxymethyl]-benzene

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Chemical Property of [(2E,6Z)-(4S,5S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-2,6-dienyloxymethyl]-benzene

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Technology Process of [(2E,6Z)-(4S,5S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-2,6-dienyloxymethyl]-benzene

There total 12 articles about [(2E,6Z)-(4S,5S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-2,6-dienyloxymethyl]-benzene 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: 97.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 321921-91-9
(2Z,6E)-(4S,5S)-8-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-octa-2,6-dien-1-ol

: 321921-92-0
[(2E,6Z)-(4S,5S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-2,6-dienyloxymethyl]-benzene

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 0.166667h;
DOI:10.1016/S0040-4020(00)00804-8

Reference yield:

: 69152-87-0
4-benzyloxycrotonaldehyde

: 321921-92-0
[(2E,6Z)-(4S,5S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-2,6-dienyloxymethyl]-benzene

Guidance literature:: Multi-step reaction with 7 steps

1.1: dibutylboron triflate / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 100 percent / CH₂Cl₂ / 1.5 h / -78 - 0 °C

2.1: Al(CH₃)3 / tetrahydrofuran; toluene / 2.5 h / 0 °C

2.2: aq. HCl / CH₂Cl₂ / 18 h / 0 °C

3.1: 14.1 g / imidazole / dimethylformamide / 18 h

4.1: 10.7 g / DIBAL / tetrahydrofuran / 1 h / -78 °C

5.1: 89 percent / potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran / 0.5 h / -78 °C

6.1: 100 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

7.1: 97 percent / imidazole / dimethylformamide / 0.17 h

With 1H-imidazole; 18-crown-6 ether; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: deprotonation / 1.2: Addition / 2.1: Substitution / 2.2: Hydrolysis / 3.1: Substitution / 4.1: Reduction / 5.1: Condensation / 6.1: Reduction / 7.1: Substitution;
DOI:10.1016/S0040-4020(00)00804-8

Reference yield:

: 251319-56-9
(2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al

: 321921-92-0
[(2E,6Z)-(4S,5S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-2,6-dienyloxymethyl]-benzene

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran / 0.5 h / -78 °C

2: 100 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

3: 97 percent / imidazole / dimethylformamide / 0.17 h

With 1H-imidazole; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Reduction / 3: Substitution;
DOI:10.1016/S0040-4020(00)00804-8