N-tert-butoxycarbonyl-N-[2-(dimethylphenylsilanyl)but-2(Z)-enyl]glycine methyl ester

Base Information

Chemical Name:N-tert-butoxycarbonyl-N-[2-(dimethylphenylsilanyl)but-2(Z)-enyl]glycine methyl ester
CAS No.:320618-86-8
Molecular Formula:C₂₀H₃₁NO₄Si
Molecular Weight:377.556
Hs Code.:

Synonyms:N-tert-butoxycarbonyl-N-[2-(dimethylphenylsilanyl)but-2(Z)-enyl]glycine methyl ester

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Chemical Property of N-tert-butoxycarbonyl-N-[2-(dimethylphenylsilanyl)but-2(Z)-enyl]glycine methyl ester

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Technology Process of N-tert-butoxycarbonyl-N-[2-(dimethylphenylsilanyl)but-2(Z)-enyl]glycine methyl ester

There total 4 articles about N-tert-butoxycarbonyl-N-[2-(dimethylphenylsilanyl)but-2(Z)-enyl]glycine methyl ester 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%

: 31954-27-5
N-(tert-butoxycarbonyl)glycine methyl ester

: 320618-66-4
1-bromo-2-(dimethylphenylsilanyl)but-2(E)-ene

: 320618-86-8
N-tert-butoxycarbonyl-N-[2-(dimethylphenylsilanyl)but-2(Z)-enyl]glycine methyl ester

Guidance literature:: With potassium hydride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1039/b506198a

Reference yield:

: 31954-27-5
N-(tert-butoxycarbonyl)glycine methyl ester

: 129158-82-3
(±)-2-(dimethylphenylsilyl)-1-buten-3-ol

: 320618-86-8
N-tert-butoxycarbonyl-N-[2-(dimethylphenylsilanyl)but-2(Z)-enyl]glycine methyl ester

Guidance literature:: (±)-2-(dimethylphenylsilyl)-1-buten-3-ol; With thionyl chloride; In diethyl ether; Inert atmosphere;

With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 0 - 20 ℃; for 14h; Inert atmosphere;

N-(tert-butoxycarbonyl)glycine methyl ester; With potassium hydride; In tetrahydrofuran; at 0 ℃; Inert atmosphere;
DOI:10.1016/j.tet.2010.04.095

Reference yield:

: 101150-39-4
E-1-iodo-1-(dimethylphenylsilyl)propene

: 320618-86-8
N-tert-butoxycarbonyl-N-[2-(dimethylphenylsilanyl)but-2(Z)-enyl]glycine methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: DIBAL / diethyl ether / 1 h / Heating

1.2: MeLi / tetrahydrofuran; diethyl ether / 0 - 20 °C

1.3: 92 percent / tetrahydrofuran; diethyl ether / 14 h / 20 °C

2.1: 90 percent / Br₂; triphenylphosphine; triethylamine / CH₂Cl₂ / 0.17 h / -20 °C

3.1: KH / tetrahydrofuran / 0 °C

3.2: 58 percent / tetrahydrofuran / 0 - 20 °C

With bromine; potassium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo0056343