N^ε-(benzyloxycarbonyl)-N^α-(tert-butoxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine methyl ester

Base Information

• Chemical Name: N^ε-(benzyloxycarbonyl)-N^α-(tert-butoxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine methyl ester
• CAS No.: 440353-76-4
• Molecular Formula: C₄₁H₆₈N₈O₉
• Molecular Weight: 817.039
• Mol file: 440353-76-4.mol

Synonyms:N^ε-(benzyloxycarbonyl)-N^α-(tert-butoxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine methyl ester

Chemical Property of N^ε-(benzyloxycarbonyl)-N^α-(tert-butoxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^ε-(benzyloxycarbonyl)-N^α-(tert-butoxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine methyl ester

There total 4 articles about N^ε-(benzyloxycarbonyl)-N^α-(tert-butoxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)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:

(S)-2-((S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-3-methyl-butyric acid (68802-93-7) + ((2R,3R)-3-Amino-2-azido-tetradecanoylamino)-acetic acid methyl ester → {(2S,3S)-2-Azido-3-[(S)-2-((S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-3-methyl-butyrylamino]-tetradecanoylamino}-acetic acid methyl ester + Nε-(benzyloxycarbonyl)-Nα-(tert-butoxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine methyl ester (440353-76-4)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20 ℃; for 54h;

DOI:10.1021/jo016276m

Reference yield:

(+/-)-trans-3-azido-4-undecyl-2-azetidinone → Nε-(benzyloxycarbonyl)-Nα-(tert-butoxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine methyl ester (440353-76-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / 4-dimethylaminopyridine / acetonitrile / 0.33 h

2: 84 percent / diisopropylethylamine; sodium azide / dimethylformamide / 20 °C

3: hydrogen chloride / diethyl ether / 0.5 h

4: 180 mg / EDAC*HCl; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 54 h / 20 °C

With hydrogenchloride; dmap; sodium azide; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo016276m

Reference yield:

(+/-)-trans-3-azido-1-(tert-butoxycarbonyl)-4-undecyl-2-azetidinone → Nε-(benzyloxycarbonyl)-Nα-(tert-butoxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine methyl ester (440353-76-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / diisopropylethylamine; sodium azide / dimethylformamide / 20 °C

2: hydrogen chloride / diethyl ether / 0.5 h

3: 180 mg / EDAC*HCl; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 54 h / 20 °C

With hydrogenchloride; sodium azide; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo016276m

upstream raw materials:

(S)-2-((S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-3-methyl-butyric acid

Downstream raw materials:

cyclo-N^ε-(benzyloxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine