N-(benzyloxycarbonyl)valylisoleucylphenylalanylprolylprolylglycyl-N^G-nitroarginine benzyl ester

Base Information

• Chemical Name: N-(benzyloxycarbonyl)valylisoleucylphenylalanylprolylprolylglycyl-N^G-nitroarginine benzyl ester
• CAS No.: 90315-71-2
• Molecular Formula: C₅₃H₇₁N₁₁O₁₂
• Molecular Weight: 1054.21
• Mol file: 90315-71-2.mol

Synonyms:N-(benzyloxycarbonyl)valylisoleucylphenylalanylprolylprolylglycyl-N^G-nitroarginine benzyl ester

Chemical Property of N-(benzyloxycarbonyl)valylisoleucylphenylalanylprolylprolylglycyl-N^G-nitroarginine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(benzyloxycarbonyl)valylisoleucylphenylalanylprolylprolylglycyl-N^G-nitroarginine benzyl ester

There total 9 articles about N-(benzyloxycarbonyl)valylisoleucylphenylalanylprolylprolylglycyl-N^G-nitroarginine benzyl 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:

N-(benzyloxycarbonyl)isoleucylphenylalanine benzyl ester (85310-51-6) → N-(benzyloxycarbonyl)valylisoleucylphenylalanylprolylprolylglycyl-NG-nitroarginine benzyl ester (90315-71-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / acetic acid, H₂ / Pd black / methanol / Ambient temperature; overnight

2: 70 percent / Et₃N / tetrahydrofuran; H₂O / 24 h / Ambient temperature

3: DCC, HONSu / DMF, -10 deg C, 1 h; r.t., 48 h

4: 92 percent / 2 M sodium hydroxide / methanol / 2 h / Ambient temperature

5: NMM, DCC, HOBt / DMF, 0 deg C, 1 h, r.t., overnight

With 4-methyl-morpholine; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; benzotriazol-1-ol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium; In tetrahydrofuran; methanol; water;

DOI:10.1246/bcsj.57.103

Reference yield:

Cbz-Ile-OH*DCHA (253595-73-2,26699-00-3) → N-(benzyloxycarbonyl)valylisoleucylphenylalanylprolylprolylglycyl-NG-nitroarginine benzyl ester (90315-71-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) NMM, ECF / 1) THF, -5 deg C, 10 min, 2) CHCl₃, 0 deg C, 1 h; r.t., overnight

2: 90 percent / acetic acid, H₂ / Pd black / methanol / Ambient temperature; overnight

3: 70 percent / Et₃N / tetrahydrofuran; H₂O / 24 h / Ambient temperature

4: DCC, HONSu / DMF, -10 deg C, 1 h; r.t., 48 h

5: 92 percent / 2 M sodium hydroxide / methanol / 2 h / Ambient temperature

6: NMM, DCC, HOBt / DMF, 0 deg C, 1 h, r.t., overnight

With 4-methyl-morpholine; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; chloroformic acid ethyl ester; benzotriazol-1-ol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium; In tetrahydrofuran; methanol; water;

DOI:10.1246/bcsj.57.103

Reference yield:

2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate (3496-11-5) → N-(benzyloxycarbonyl)valylisoleucylphenylalanylprolylprolylglycyl-NG-nitroarginine benzyl ester (90315-71-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / Et₃N / tetrahydrofuran; H₂O / 24 h / Ambient temperature

2: DCC, HONSu / DMF, -10 deg C, 1 h; r.t., 48 h

3: 92 percent / 2 M sodium hydroxide / methanol / 2 h / Ambient temperature

4: NMM, DCC, HOBt / DMF, 0 deg C, 1 h, r.t., overnight

With 4-methyl-morpholine; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; water;

DOI:10.1246/bcsj.57.103

upstream raw materials:

N^G-nitroarginine benzyl ester

N-(benzyloxycarbonyl)valylisoleucylphenylalanylprolylprolylglycine

2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate

N-tert-butoxycarbonyl-L-prolyl-L-proline

Refernces