(E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3,3-diethoxypropyl)carbamate

Base Information

• Chemical Name: (E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3,3-diethoxypropyl)carbamate
• CAS No.: 1305173-66-3
• Molecular Formula: C₃₄H₅₁NO₅Si
• Molecular Weight: 581.868
• Mol file: 1305173-66-3.mol

Synonyms:(E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3,3-diethoxypropyl)carbamate

Chemical Property of (E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3,3-diethoxypropyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3,3-diethoxypropyl)carbamate

There total 1 articles about (E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3,3-diethoxypropyl)carbamate 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: 71.0%

2-bromo-1-tert-butyldiphenylsilyloxyprop-2-ene + potassium (E)-tert-butyl 3-trifluoroboratoallyl(3,3-diethoxypropyl)carbamate → (E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3,3-diethoxypropyl)carbamate (1305173-66-3)

Guidance literature:

With palladium diacetate; caesium carbonate; triphenylphosphine; In tetrahydrofuran; water; at 70 ℃; for 3h;

DOI:10.1016/j.tetlet.2010.11.162

Reference yield:

(E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3,3-diethoxypropyl)carbamate (1305173-66-3) → (E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3-oxopropyl)carbamate (1305173-69-6)

Guidance literature:

With Amberlyst 15; In water; acetone; for 3h;

DOI:10.1016/j.tetlet.2010.11.162

Reference yield:

(E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3,3-diethoxypropyl)carbamate (1305173-66-3) → (4aRS,5SR,8aSR)-tert-butyl 5-((benzylamino)methyl)-7-((tert-butyldimethylsilyloxy)methyl)-1,4,4a,5,6,8a-hexahydroisoquinoline-2(3H)-carboxylate

Guidance literature:

Multi-step reaction with 6 steps

1: Amberlyst_.(R). 15 / water; acetone / 3 h

2: chloroform / 9 h / 60 °C

3: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C

4: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 24 h / Reflux

5: sodium triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C

6: 1H-imidazole / dichloromethane / 20 °C

With 1H-imidazole; 2,6-di-tert-butyl-4-methyl-phenol; sodium triacetoxyborohydride; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane; chloroform; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; 2: Wittig reaction / 4: Diels-Alder reaction;

DOI:10.1016/j.tetlet.2010.11.162

Downstream raw materials:

(E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3-oxopropyl)carbamate

tert-butyl (E)-4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl((E)-5-oxopent-3-enyl)carbamate