(3S)-(E)-N-Boc-N-[2-[5-(2,2-dimethyl-propanoyl-oxy)-2-(3-tert-butyl dimethylsilyloxy-but-1-enyl)-4-methoxy-phenyl]ethyl]-amine

Base Information

• Chemical Name: (3S)-(E)-N-Boc-N-[2-[5-(2,2-dimethyl-propanoyl-oxy)-2-(3-tert-butyl dimethylsilyloxy-but-1-enyl)-4-methoxy-phenyl]ethyl]-amine
• CAS No.: 1344720-71-3
• Molecular Formula: C₂₉H₄₉NO₆Si
• Molecular Weight: 535.797
• Mol file: 1344720-71-3.mol

Synonyms:(3S)-(E)-N-Boc-N-[2-[5-(2,2-dimethyl-propanoyl-oxy)-2-(3-tert-butyl dimethylsilyloxy-but-1-enyl)-4-methoxy-phenyl]ethyl]-amine

Chemical Property of (3S)-(E)-N-Boc-N-[2-[5-(2,2-dimethyl-propanoyl-oxy)-2-(3-tert-butyl dimethylsilyloxy-but-1-enyl)-4-methoxy-phenyl]ethyl]-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-(E)-N-Boc-N-[2-[5-(2,2-dimethyl-propanoyl-oxy)-2-(3-tert-butyl dimethylsilyloxy-but-1-enyl)-4-methoxy-phenyl]ethyl]-amine

There total 6 articles about (3S)-(E)-N-Boc-N-[2-[5-(2,2-dimethyl-propanoyl-oxy)-2-(3-tert-butyl dimethylsilyloxy-but-1-enyl)-4-methoxy-phenyl]ethyl]-amine 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: 87.0%

(S,E)-tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-yl)oxy)silane (1198272-03-5) + N-Boc-N-[2-(2-bromo-5-(2,2-dimethylpropanoyloxy)-4-methoxyphenyl)ethyl]amine (1344720-58-6) → (3S)-(E)-N-Boc-N-[2-[5-(2,2-dimethyl-propanoyl-oxy)-2-(3-tert-butyl dimethylsilyloxy-but-1-enyl)-4-methoxy-phenyl]ethyl]-amine (1344720-71-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate; In 1,4-dioxane; water; at 80 ℃; for 2h; optical yield given as %ee; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.033

Reference yield:

4-bromo-5-bromomethyl-2-methoxyphenol (222622-91-5) → (3S)-(E)-N-Boc-N-[2-[5-(2,2-dimethyl-propanoyl-oxy)-2-(3-tert-butyl dimethylsilyloxy-but-1-enyl)-4-methoxy-phenyl]ethyl]-amine (1344720-71-3)

Guidance literature:

Multi-step reaction with 4 steps

1: dimethyl sulfoxide / 0.08 h / 20 °C / Inert atmosphere

2: pyridine; dmap / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere

3: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 1 h / 0 - 20 °C / Inert atmosphere

4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere

With pyridine; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; nickel(II) chloride hexahydrate; sodium hydrogencarbonate; In 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; 4: Suzuki-Miyaura coupling;

DOI:10.1016/j.tet.2011.09.033

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3S)-(E)-N-Boc-N-[2-[5-(2,2-dimethyl-propanoyl-oxy)-2-(3-tert-butyl dimethylsilyloxy-but-1-enyl)-4-methoxy-phenyl]ethyl]-amine (1344720-71-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 1 h / 0 - 20 °C / Inert atmosphere

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; nickel(II) chloride hexahydrate; sodium hydrogencarbonate; In 1,4-dioxane; methanol; water; 2: Suzuki-Miyaura coupling;

DOI:10.1016/j.tet.2011.09.033

upstream raw materials:

(S,E)-tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-yl)oxy)silane

N-Boc-N-[2-(2-bromo-5-(2,2-dimethylpropanoyloxy)-4-methoxyphenyl)ethyl]amine

4-bromo-5-bromomethyl-2-methoxyphenol

2-bromo-5-(2,2-dimethylpropanoyloxy)-4-methoxy-phenyl-acetonitrile

Downstream raw materials:

(3S)-(E)-N-Boc-N-[2-[5-(2,2-dimethyl-propanoyl-oxy)-2-(3-hydroxybut-1-enyl)-4-methoxy-phenyl]ethyl]amine

oleracein E

(-)-trolline