N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyldi(glycyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)glycine methyl ester

Base Information

• Chemical Name: N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyldi(glycyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)glycine methyl ester
• CAS No.: 117652-68-3
• Molecular Formula: C₅₄H₇₅N₉O₁₅
• Molecular Weight: 1090.24

Synonyms:N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyldi(glycyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)glycine methyl ester

Chemical Property of N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyldi(glycyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)glycine methyl ester

Chemical Property:

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Technology Process of N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyldi(glycyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)glycine methyl ester

There total 3 articles about N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyldi(glycyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)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: 84.0%

N2-(tert-butoxycarbonyl)-N5-acetyl-N5-(benzyloxy)-L-ornithylglycine (117678-52-1) + ((S)-5-(Acetyl-benzyloxy-amino)-2-{2-[(S)-5-(acetyl-benzyloxy-amino)-2-amino-pentanoylamino]-acetylamino}-pentanoylamino)-acetic acid methyl ester; compound with trifluoro-acetic acid (117652-67-2) → N2-(tert-butoxycarbonyl)-N5-acetyl-N5-(benzyloxy)-L-ornithyldi(glycyl-N5-acetyl-N5-(benzyloxy)-L-ornithyl)glycine methyl ester (117652-68-3)

Guidance literature:

With 4-methyl-morpholine; 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; for 48h; Ambient temperature;

DOI:10.1021/jo00261a019

Reference yield:

N2-(tert-butoxycarbonyl)-N5-acetyl-N5-(benzyloxy)-L-ornithine (52816-29-2) → N2-(tert-butoxycarbonyl)-N5-acetyl-N5-(benzyloxy)-L-ornithyldi(glycyl-N5-acetyl-N5-(benzyloxy)-L-ornithyl)glycine methyl ester (117652-68-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / dicyclohexylcarbodiimide (DCC), N-methylmorpholine, 1-hydroxybenzotriazole (HOBt) / dimethylformamide / 48 h / Ambient temperature

2: 95 percent / 1 N NaOH / acetone / 0.25 h / 0 °C

3: 84 percent / dicyclohexylcarbodiimide (DCC), N-methylmorpholine, N-hydroxysuccinimide (HOSu) / dimethylformamide / 48 h / Ambient temperature

With 4-methyl-morpholine; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00261a019

Reference yield:

N2-(tert-butoxycarbonyl)-N5-acetyl-N5-(benzyloxy)-L-ornithylglycine methyl ester (117652-62-7) → N2-(tert-butoxycarbonyl)-N5-acetyl-N5-(benzyloxy)-L-ornithyldi(glycyl-N5-acetyl-N5-(benzyloxy)-L-ornithyl)glycine methyl ester (117652-68-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / 1 N NaOH / acetone / 0.25 h / 0 °C

2: 84 percent / dicyclohexylcarbodiimide (DCC), N-methylmorpholine, N-hydroxysuccinimide (HOSu) / dimethylformamide / 48 h / Ambient temperature

With 4-methyl-morpholine; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00261a019

upstream raw materials:

N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithylglycine

((S)-5-(Acetyl-benzyloxy-amino)-2-{2-[(S)-5-(acetyl-benzyloxy-amino)-2-amino-pentanoylamino]-acetylamino}-pentanoylamino)-acetic acid methyl ester; compound with trifluoro-acetic acid

N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine

N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithylglycine methyl ester

Downstream raw materials:

cyclotri(N⁵-acetyl-N⁵-(benzyloxy)-L-ornithylglycyl)

C₅₇H₇₆N₁₀O₁₇

{(S)-5-(Acetyl-benzyloxy-amino)-2-[2-((S)-5-(acetyl-benzyloxy-amino)-2-{2-[(S)-5-(acetyl-benzyloxy-amino)-2-tert-butoxycarbonylamino-pentanoylamino]-acetylamino}-pentanoylamino)-acetylamino]-pentanoylamino}-acetic acid

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