1-[4-bromo-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-3-[1-(tert-butyl-dimethyl-silanyloxy)-3-triethylsilanyloxy-propyl]-benzene

Base Information

Chemical Name:1-[4-bromo-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-3-[1-(tert-butyl-dimethyl-silanyloxy)-3-triethylsilanyloxy-propyl]-benzene
CAS No.:850005-86-6
Molecular Formula:C₃₁H₅₇BrO₃Si₃
Molecular Weight:641.952
Hs Code.:

1-[4-bromo-1-(<i>tert</i>-butyl-dimethyl-silanyloxy)-but-3-ynyl]-3-[1-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-triethylsilanyloxy-propyl]-benzene

Synonyms:1-[4-bromo-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-3-[1-(tert-butyl-dimethyl-silanyloxy)-3-triethylsilanyloxy-propyl]-benzene

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Chemical Property of 1-[4-bromo-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-3-[1-(tert-butyl-dimethyl-silanyloxy)-3-triethylsilanyloxy-propyl]-benzene

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Technology Process of 1-[4-bromo-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-3-[1-(tert-butyl-dimethyl-silanyloxy)-3-triethylsilanyloxy-propyl]-benzene

There total 11 articles about 1-[4-bromo-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-3-[1-(tert-butyl-dimethyl-silanyloxy)-3-triethylsilanyloxy-propyl]-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: 93.0%

: 850005-71-9
1-((1S)-1-(tert-butyldimethylsilyloxy)-3-butynyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)-3-(triethylsilyloxy)propyl]benzene

: 850005-86-6
1-[4-bromo-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-3-[1-(tert-butyl-dimethyl-silanyloxy)-3-triethylsilanyloxy-propyl]-benzene

Guidance literature:: 1-((1S)-1-(tert-butyldimethylsilyloxy)-3-butynyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)-3-(triethylsilyloxy)propyl]benzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -40 ℃; for 1h;

With bromocyane; In tetrahydrofuran; hexane; at -78 - -40 ℃;
DOI:10.1016/j.tet.2005.01.062

Reference yield:

: 850005-76-4
methyl (3R)-3-(3-formylphenyl)-3-(tert-butyldimethylsillyloxy)propanoate

: 850005-86-6
1-[4-bromo-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-3-[1-(tert-butyl-dimethyl-silanyloxy)-3-triethylsilanyloxy-propyl]-benzene

Guidance literature:: Multi-step reaction with 4 steps

1.1: (+)-diisopropyl tartrate; molecular sieves A₄ / toluene / -78 °C

1.2: toluene / 20 h / -78 °C

1.3: 1.28 g / imidazole / dimethylformamide / 4 h / 20 °C

2.1: DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

2.2: 86 percent / sodium borohydride / methanol / 1 h / 20 °C

3.1: 100 percent / imidazole / dimethylformamide / 5 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

4.2: 93 percent / cyanogen bromide / tetrahydrofuran; hexane / -78 - -40 °C

With 1H-imidazole; n-butyllithium; L-(+)-diisopropyl tartrate; 4 A molecular sieve; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2005.01.062

Reference yield:

: 3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxymethyl-phenyl)-propionic acid methyl ester

: 850005-86-6
1-[4-bromo-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-3-[1-(tert-butyl-dimethyl-silanyloxy)-3-triethylsilanyloxy-propyl]-benzene

Guidance literature:: Multi-step reaction with 5 steps

1.1: 28.0 mg / 2-iodoxybenzoic acid / dimethylsulfoxide; tetrahydrofuran / 0.5 h / 20 °C

2.1: (+)-diisopropyl tartrate; molecular sieves A₄ / toluene / -78 °C

2.2: toluene / 20 h / -78 °C

2.3: 1.28 g / imidazole / dimethylformamide / 4 h / 20 °C

3.1: DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

3.2: 86 percent / sodium borohydride / methanol / 1 h / 20 °C

4.1: 100 percent / imidazole / dimethylformamide / 5 h / 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

5.2: 93 percent / cyanogen bromide / tetrahydrofuran; hexane / -78 - -40 °C

With 1H-imidazole; n-butyllithium; L-(+)-diisopropyl tartrate; 4 A molecular sieve; diisobutylaluminium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2005.01.062