N-(tert-butoxycarbonyl)-2-[3-benzyloxymethyl-4-(tert-butyldimethylsilyloxy)-1,2-butadienyl]aniline

Base Information

Chemical Name:N-(tert-butoxycarbonyl)-2-[3-benzyloxymethyl-4-(tert-butyldimethylsilyloxy)-1,2-butadienyl]aniline
CAS No.:1314559-50-6
Molecular Formula:C₂₉H₄₁NO₄Si
Molecular Weight:495.734
Hs Code.:

Synonyms:N-(tert-butoxycarbonyl)-2-[3-benzyloxymethyl-4-(tert-butyldimethylsilyloxy)-1,2-butadienyl]aniline

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Chemical Property of N-(tert-butoxycarbonyl)-2-[3-benzyloxymethyl-4-(tert-butyldimethylsilyloxy)-1,2-butadienyl]aniline

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Technology Process of N-(tert-butoxycarbonyl)-2-[3-benzyloxymethyl-4-(tert-butyldimethylsilyloxy)-1,2-butadienyl]aniline

There total 3 articles about N-(tert-butoxycarbonyl)-2-[3-benzyloxymethyl-4-(tert-butyldimethylsilyloxy)-1,2-butadienyl]aniline 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:

: C₁₉H₃₀O₅SSi

: 161117-84-6
tert-butyl 2-iodophenylcarbamate

: 1314559-50-6
N-(tert-butoxycarbonyl)-2-[3-benzyloxymethyl-4-(tert-butyldimethylsilyloxy)-1,2-butadienyl]aniline

Guidance literature:: C₁₉H₃₀O₅SSi; With n-butyllithium; copper(I) bromide dimethylsulfide complex; tri-n-butyl-tin hydride; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h; Inert atmosphere;

tert-butyl 2-iodophenylcarbamate; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; trifuran-2-yl-phosphane; In N,N-dimethyl-formamide; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1016/j.tet.2011.05.064

Reference yield:

: 1314558-99-0
1-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-3-butyn-2-ol

: 1314559-50-6
N-(tert-butoxycarbonyl)-2-[3-benzyloxymethyl-4-(tert-butyldimethylsilyloxy)-1,2-butadienyl]aniline

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.1: copper(I) bromide dimethylsulfide complex; n-butyllithium; tri-n-butyl-tin hydride; diisopropylamine / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

2.2: 4 h / 20 °C / Inert atmosphere

With n-butyllithium; copper(I) bromide dimethylsulfide complex; tri-n-butyl-tin hydride; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 2.2: Stille coupling;
DOI:10.1016/j.tet.2011.05.064

Reference yield:

: 154458-57-8
1-benzyloxy-3-(tert-butyldimethylsilyloxy)propan-2-one

: 1314559-50-6
N-(tert-butoxycarbonyl)-2-[3-benzyloxymethyl-4-(tert-butyldimethylsilyloxy)-1,2-butadienyl]aniline

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran; diethyl ether / 1.5 h / 0 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.1: copper(I) bromide dimethylsulfide complex; n-butyllithium; tri-n-butyl-tin hydride; diisopropylamine / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

3.2: 4 h / 20 °C / Inert atmosphere

With n-butyllithium; copper(I) bromide dimethylsulfide complex; tri-n-butyl-tin hydride; triethylamine; diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 3.2: Stille coupling;
DOI:10.1016/j.tet.2011.05.064