benzyl(13-bromo-8-((tert-butyldimethylsilyl)oxy)tetradeca-13-en-1,6-diyn-1-yl)dimethylsilane

Base Information

Chemical Name:benzyl(13-bromo-8-((tert-butyldimethylsilyl)oxy)tetradeca-13-en-1,6-diyn-1-yl)dimethylsilane
CAS No.:1415667-49-0
Molecular Formula:C₂₉H₄₅BrOSi₂
Molecular Weight:545.751
Hs Code.:

Synonyms:benzyl(13-bromo-8-((tert-butyldimethylsilyl)oxy)tetradeca-13-en-1,6-diyn-1-yl)dimethylsilane

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Chemical Property of benzyl(13-bromo-8-((tert-butyldimethylsilyl)oxy)tetradeca-13-en-1,6-diyn-1-yl)dimethylsilane

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Technology Process of benzyl(13-bromo-8-((tert-butyldimethylsilyl)oxy)tetradeca-13-en-1,6-diyn-1-yl)dimethylsilane

There total 9 articles about benzyl(13-bromo-8-((tert-butyldimethylsilyl)oxy)tetradeca-13-en-1,6-diyn-1-yl)dimethylsilane 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%

: 1415667-44-5
14-(benzyldimethylsilyl)-2-bromotetradeca-1-en-8,13-diyn-7-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1415667-49-0
benzyl(13-bromo-8-((tert-butyldimethylsilyl)oxy)tetradeca-13-en-1,6-diyn-1-yl)dimethylsilane

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol303041j

Reference yield:

: 93184-64-6
hept-6-yn-1-yl acetate

: 1415667-49-0
benzyl(13-bromo-8-((tert-butyldimethylsilyl)oxy)tetradeca-13-en-1,6-diyn-1-yl)dimethylsilane

Guidance literature:: Multi-step reaction with 5 steps

1.1: boron tribromide / dichloromethane / 5 h / 20 °C / Inert atmosphere

2.1: potassium carbonate / methanol / 2 h / Inert atmosphere

3.1: triethylamine; dimethyl sulfoxide; sulfur trioxide pyridine complex / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

4.2: 2 h / -78 - 20 °C / Inert atmosphere

5.1: dmap; 1H-imidazole / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; sulfur trioxide pyridine complex; boron tribromide; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ol303041j

Reference yield:

: 1833-31-4
benzyl(chloro)dimethylsilane

: 1415667-49-0
benzyl(13-bromo-8-((tert-butyldimethylsilyl)oxy)tetradeca-13-en-1,6-diyn-1-yl)dimethylsilane

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 - 20 °C / Inert atmosphere

3.1: dmap; 1H-imidazole / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol303041j