N²-Z-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine

Base Information

• Chemical Name: N²-Z-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine
• CAS No.: 250215-21-5
• Molecular Formula: C₃₅H₅₀N₆O₁₅
• Molecular Weight: 794.813

Synonyms:N²-Z-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine

Chemical Property of N²-Z-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine

Chemical Property:

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Technology Process of N²-Z-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine

There total 8 articles about N²-Z-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine 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: 93.0%

acetic anhydride (108-24-7) + 2-{2-[2-(benzyloxycarbonylamino)-5-(hydroxyamino)-valerylamino]-5-(hydroxyamino)valerylamino}-5-(hydroxyamino)valeric acid trihydrochloride → N2-Z-N5-acetyl-N5-O-acetyl-L-ornithyl-N5-acetyl-N5-O-acetyl-L-ornithyl-N5-acetyl-N5-O-acetyl-L-ornithine (250215-21-5)

Guidance literature:

With potassium acetate; potassium hydrogencarbonate; acetic acid; at 20 ℃; for 4.5h; pH=4;

DOI:10.1021/jo990769y

Reference yield:

Nδ-(tert-butoxycarbonyl)-L-ornithine (13650-49-2,184576-63-4) → N2-Z-N5-acetyl-N5-O-acetyl-L-ornithyl-N5-acetyl-N5-O-acetyl-L-ornithyl-N5-acetyl-N5-O-acetyl-L-ornithine (250215-21-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dicyclohexyl-carbodiimide; 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate / water; tetrahydrofuran / 24 h

1.2: 24 h

2.1: acetic acid / 1 h

3.1: potassium hydroxide / methanol / 24 h

4.1: 3-chloro-benzenecarboperoxoic acid / methanol / 1 h / 0 °C

5.1: trifluoroacetic acid / dichloromethane / 1 h

5.2: 1 h

6.1: potassium hydrogencarbonate; potassium hydroxide / 4 h / pH 4

With 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; potassium hydrogencarbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jacs.9b05874

Reference yield:

Z-Orn(Boc)-OH (7733-29-1,199924-46-4) → N2-Z-N5-acetyl-N5-O-acetyl-L-ornithyl-N5-acetyl-N5-O-acetyl-L-ornithyl-N5-acetyl-N5-O-acetyl-L-ornithine (250215-21-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dicyclohexyl-carbodiimide; 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate / water; tetrahydrofuran / 24 h

1.2: 24 h

2.1: acetic acid / 1 h

3.1: potassium hydroxide / methanol / 24 h

4.1: 3-chloro-benzenecarboperoxoic acid / methanol / 1 h / 0 °C

5.1: trifluoroacetic acid / dichloromethane / 1 h

5.2: 1 h

6.1: potassium hydrogencarbonate; potassium hydroxide / 4 h / pH 4

With 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; potassium hydrogencarbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jacs.9b05874

upstream raw materials:

acetic anhydride

N^δ-(tert-butoxycarbonyl)-L-ornithine

Z-Orn(Boc)-OH

(S)-2-{(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tertbutoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valerylamino}-5-(tert-butoxycarbonylamino)valeric acid

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