2-((E)-(S)-1-Hydroxy-3-methyl-hexa-2,5-dienyl)-4-methoxy-5-((Z)-2-methyl-7-triisopropylsilanyl-hept-2-en-6-ynyl)-phenol

Base Information

Chemical Name:2-((E)-(S)-1-Hydroxy-3-methyl-hexa-2,5-dienyl)-4-methoxy-5-((Z)-2-methyl-7-triisopropylsilanyl-hept-2-en-6-ynyl)-phenol
CAS No.:403696-86-6
Molecular Formula:C₃₁H₄₈O₃Si
Molecular Weight:496.806
Hs Code.:

Synonyms:2-((E)-(S)-1-Hydroxy-3-methyl-hexa-2,5-dienyl)-4-methoxy-5-((Z)-2-methyl-7-triisopropylsilanyl-hept-2-en-6-ynyl)-phenol

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Chemical Property of 2-((E)-(S)-1-Hydroxy-3-methyl-hexa-2,5-dienyl)-4-methoxy-5-((Z)-2-methyl-7-triisopropylsilanyl-hept-2-en-6-ynyl)-phenol

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Technology Process of 2-((E)-(S)-1-Hydroxy-3-methyl-hexa-2,5-dienyl)-4-methoxy-5-((Z)-2-methyl-7-triisopropylsilanyl-hept-2-en-6-ynyl)-phenol

There total 17 articles about 2-((E)-(S)-1-Hydroxy-3-methyl-hexa-2,5-dienyl)-4-methoxy-5-((Z)-2-methyl-7-triisopropylsilanyl-hept-2-en-6-ynyl)-phenol 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:

: 31558-41-5
4-bromo-2,5-dimethoxybenzaldehyde

: 403696-86-6
2-((E)-(S)-1-Hydroxy-3-methyl-hexa-2,5-dienyl)-4-methoxy-5-((Z)-2-methyl-7-triisopropylsilanyl-hept-2-en-6-ynyl)-phenol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 100 percent / sodium borohydride / methanol / 0 - 20 °C

2.1: 95 percent / phosphorous tribromide / CH₂Cl₂ / 1 h / 0 - 20 °C

3.1: zinc; dibromoethane / tetrahydrofuran / 0.83 h / 0 °C

3.2: 98 percent / palladium tetrakis(triphenylphosphine) / tetrahydrofuran / 27 h / 23 °C

4.1: n-butyllithium / diethyl ether; hexane / 0.75 h / -78 °C

4.2: 94 percent / diethyl ether / -78 - 35 °C

5.1: borontribromide / CH₂Cl₂ / 16 h / -78 - 23 °C

6.1: 5.53 g / diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: tert-butyllithium / diethyl ether; pentane / 1 h / -78 °C

7.2: ZnBr₂; (1S,2R)-N-methylephedrine; n-butyllithium / diethyl ether; toluene; hexane / 1 h / 0 °C

7.3: 91 percent / toluene; diethyl ether / 1 h / 0 °C

8.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

9.1: H₂; quinoline / Pd/BaSO₄ / methanol; hexane / 4.67 h / 23 °C / 760.05 Torr

With quinoline; sodium tetrahydroborate; n-butyllithium; 1,1-Dibromoethane; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; boron tribromide; phosphorus tribromide; N-ethyl-N,N-diisopropylamine; zinc; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; pentane; 9.1: Lindlar hydrogenation;
DOI:10.1021/ja016585u

Reference yield:

: 403696-85-5
2-((E)-(S)-1-Hydroxy-3-methyl-hex-2-en-5-ynyl)-4-methoxy-5-((Z)-2-methyl-7-triisopropylsilanyl-hept-2-en-6-ynyl)-phenol

: 403696-86-6
2-((E)-(S)-1-Hydroxy-3-methyl-hexa-2,5-dienyl)-4-methoxy-5-((Z)-2-methyl-7-triisopropylsilanyl-hept-2-en-6-ynyl)-phenol

Guidance literature:: With quinoline; hydrogen; Pd-BaSO₄; In methanol; hexane; at 23 ℃; for 4.66667h; under 760.051 Torr;
DOI:10.1021/ja016585u

Reference yield:

: 403696-81-1
5-(triisopropylsilyl)-4-pentyn-1-al

: 403696-86-6
2-((E)-(S)-1-Hydroxy-3-methyl-hexa-2,5-dienyl)-4-methoxy-5-((Z)-2-methyl-7-triisopropylsilanyl-hept-2-en-6-ynyl)-phenol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 2.044 g / tetrahydrofuran / 0.17 h / -20 °C

2.1: zinc; dibromoethane / tetrahydrofuran / 0.83 h / 0 °C

2.2: 98 percent / palladium tetrakis(triphenylphosphine) / tetrahydrofuran / 27 h / 23 °C

3.1: n-butyllithium / diethyl ether; hexane / 0.75 h / -78 °C

3.2: 94 percent / diethyl ether / -78 - 35 °C

4.1: borontribromide / CH₂Cl₂ / 16 h / -78 - 23 °C

5.1: 5.53 g / diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: tert-butyllithium / diethyl ether; pentane / 1 h / -78 °C

6.2: ZnBr₂; (1S,2R)-N-methylephedrine; n-butyllithium / diethyl ether; toluene; hexane / 1 h / 0 °C

6.3: 91 percent / toluene; diethyl ether / 1 h / 0 °C

7.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

8.1: H₂; quinoline / Pd/BaSO₄ / methanol; hexane / 4.67 h / 23 °C / 760.05 Torr

With quinoline; n-butyllithium; 1,1-Dibromoethane; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; boron tribromide; N-ethyl-N,N-diisopropylamine; zinc; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; pentane; 8.1: Lindlar hydrogenation;
DOI:10.1021/ja016585u