(2E)-N-[6-(tert-butyldimethylsilyloxymethyl)-11-({4-oxo-4-[phenyl(pyridin-4-ylmethyl)amino]butanoyl}amino)undecyl]-N'-(2,2-diphenylethyl)but-2-enediamide

Base Information

• Chemical Name: (2E)-N-[6-(tert-butyldimethylsilyloxymethyl)-11-({4-oxo-4-[phenyl(pyridin-4-ylmethyl)amino]butanoyl}amino)undecyl]-N'-(2,2-diphenylethyl)but-2-enediamide
• CAS No.: 883981-66-6
• Molecular Formula: C₅₂H₇₁N₅O₅Si
• Molecular Weight: 874.252
• Mol file: 883981-66-6.mol

Synonyms:(2E)-N-[6-(tert-butyldimethylsilyloxymethyl)-11-({4-oxo-4-[phenyl(pyridin-4-ylmethyl)amino]butanoyl}amino)undecyl]-N'-(2,2-diphenylethyl)but-2-enediamide

Chemical Property of (2E)-N-[6-(tert-butyldimethylsilyloxymethyl)-11-({4-oxo-4-[phenyl(pyridin-4-ylmethyl)amino]butanoyl}amino)undecyl]-N'-(2,2-diphenylethyl)but-2-enediamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E)-N-[6-(tert-butyldimethylsilyloxymethyl)-11-({4-oxo-4-[phenyl(pyridin-4-ylmethyl)amino]butanoyl}amino)undecyl]-N'-(2,2-diphenylethyl)but-2-enediamide

There total 11 articles about (2E)-N-[6-(tert-butyldimethylsilyloxymethyl)-11-({4-oxo-4-[phenyl(pyridin-4-ylmethyl)amino]butanoyl}amino)undecyl]-N'-(2,2-diphenylethyl)but-2-enediamide 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:

(11-amino-6-hydroxymethyl-undecyl)-carbamic acid benzyl ester → (2E)-N-[6-(tert-butyldimethylsilyloxymethyl)-11-({4-oxo-4-[phenyl(pyridin-4-ylmethyl)amino]butanoyl}amino)undecyl]-N'-(2,2-diphenylethyl)but-2-enediamide (883981-66-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1.10 g / Et₃N / CH₂Cl₂ / 0.75 h

2.1: H₂; HCl / Pd/C / diethyl ether; methanol / atmospheric pressure

3.1: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate; triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

3.2: 550 mg / triethylamine / CH₂Cl₂ / 4 h / 20 °C

4.1: 63 percent / imidazole / CH₂Cl₂ / 2 h

5.1: piperidine / tetrahydrofuran; acetonitrile / 2.5 h / 20 °C

6.1: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate; triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

6.2: 20.0 mg / triethylamine / CH₂Cl₂; tetrahydrofuran / 14 h / 20 °C

With piperidine; 1H-imidazole; hydrogenchloride; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/ja057664z

Reference yield:

methyl 7-{[(allyloxy)carbonyl]amino}-2-(5-{[(benzyloxy)carbonyl]amino}pentyl)heptanoate (883981-59-7) → (2E)-N-[6-(tert-butyldimethylsilyloxymethyl)-11-({4-oxo-4-[phenyl(pyridin-4-ylmethyl)amino]butanoyl}amino)undecyl]-N'-(2,2-diphenylethyl)but-2-enediamide (883981-66-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 68 percent / diisobutylaluminum hydride / toluene; tetrahydrofuran / 4 h / -78 °C

2.1: phenylsilane; Pd(PPh₃)4 / CH₂Cl₂ / 0.75 h

3.1: 1.10 g / Et₃N / CH₂Cl₂ / 0.75 h

4.1: H₂; HCl / Pd/C / diethyl ether; methanol / atmospheric pressure

5.1: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate; triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

5.2: 550 mg / triethylamine / CH₂Cl₂ / 4 h / 20 °C

6.1: 63 percent / imidazole / CH₂Cl₂ / 2 h

7.1: piperidine / tetrahydrofuran; acetonitrile / 2.5 h / 20 °C

8.1: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate; triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

8.2: 20.0 mg / triethylamine / CH₂Cl₂; tetrahydrofuran / 14 h / 20 °C

With piperidine; 1H-imidazole; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; phenylsilane; hydrogen; diisobutylaluminium hydride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja057664z

Reference yield:

allyl benzyl [6-(hydroxymethyl)undecane-1,11-diyl]biscarbamate (883981-60-0) → (2E)-N-[6-(tert-butyldimethylsilyloxymethyl)-11-({4-oxo-4-[phenyl(pyridin-4-ylmethyl)amino]butanoyl}amino)undecyl]-N'-(2,2-diphenylethyl)but-2-enediamide (883981-66-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: phenylsilane; Pd(PPh₃)4 / CH₂Cl₂ / 0.75 h

2.1: 1.10 g / Et₃N / CH₂Cl₂ / 0.75 h

3.1: H₂; HCl / Pd/C / diethyl ether; methanol / atmospheric pressure

4.1: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate; triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

4.2: 550 mg / triethylamine / CH₂Cl₂ / 4 h / 20 °C

5.1: 63 percent / imidazole / CH₂Cl₂ / 2 h

6.1: piperidine / tetrahydrofuran; acetonitrile / 2.5 h / 20 °C

7.1: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate; triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

7.2: 20.0 mg / triethylamine / CH₂Cl₂; tetrahydrofuran / 14 h / 20 °C

With piperidine; 1H-imidazole; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; phenylsilane; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/ja057664z

upstream raw materials:

4-oxo-4-[phenyl(pyridin-4-ylmethyl)amino]butanoic acid

methyl 7-{[(allyloxy)carbonyl]amino}-2-(5-{[(benzyloxy)carbonyl]amino}pentyl)heptanoate

allyl benzyl [6-(hydroxymethyl)undecane-1,11-diyl]biscarbamate

dimethyl (5-{[(allyloxy)carbonyl]amino}pentyl)(5-{[(benzyloxy)carbonyl]amino}pentyl)malonate