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

Base Information

• Chemical Name: N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine
• CAS No.: 52816-29-2
• Molecular Formula: C₁₉H₂₈N₂O₆
• Molecular Weight: 380.441
• Mol file: 52816-29-2.mol

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

Chemical Property of N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine

There total 28 articles about N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-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: 85.0%

di-tert-butyl dicarbonate (24424-99-5) + N5-Acetyl-N5-benzyloxy-L-ornithin (52816-28-1) → N2-(tert-butoxycarbonyl)-N5-acetyl-N5-(benzyloxy)-L-ornithine (52816-29-2)

Guidance literature:

With triethylamine; In tetrahydrofuran; water; for 16h; Ambient temperature;

DOI:10.1021/jo00187a023

Reference yield: 54.0%

di-tert-butyl oxalate (691-64-5) + N5-Acetyl-N5-benzyloxy-L-ornithin (52816-28-1) → N2-(tert-butoxycarbonyl)-N5-acetyl-N5-(benzyloxy)-L-ornithine (52816-29-2)

Guidance literature:

With 4-methyl-morpholine; In 1,4-dioxane; water; 1.) 5 deg C, 5 h; 2.) 25 deg C, 16 h;

DOI:10.1002/jlac.198419840804

Reference yield:

N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2) → N2-(tert-butoxycarbonyl)-N5-acetyl-N5-(benzyloxy)-L-ornithine (52816-29-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NEt₃, 2.) NaBH₄ / 1.) THF, 1 h, -5 deg C, 2.) H₂O, 4 h, 0 deg C -> room temperature

2: 66 percent / PPh₃, DEAD / tetrahydrofuran / 5 h / Ambient temperature

3: 55 percent / H₂ / 5percent Pd/C / ethyl acetate / 760 Torr / 1.) 1.5 h, 0 deg C, 2.) 2.5 h, room temperature

4: 57 percent / CF₃COOH / 1 h / Ambient temperature

5: 85 percent / NEt₃ / tetrahydrofuran; H₂O / 16 h / Ambient temperature

With sodium tetrahydroborate; hydrogen; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; water; ethyl acetate;

DOI:10.1021/jo00187a023

upstream raw materials:

di-tert-butyl oxalate

N⁵-Acetyl-N⁵-benzyloxy-L-ornithin

di-tert-butyl dicarbonate

1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate

Downstream raw materials:

(S)-5-(Acetyl-benzyloxy-amino)-2-amino-pentanoic acid methyl ester

N,N’-{[(2S,5S)-3,6-dioxopiperazine-2,5-diyl]bis(propane-3,1-diyl)}bis[N-(benzyloxy)acetamide]

N,N’-{[(2S,5S)-3,6-dioxopiperazine-2,5-diyl]bis(propane-3,1-diyl)}bis(N-hydroxyacetamide)

(N⁵-Acetyl-N⁵-benzyloxy-L-ornithyl)-N⁵-acetyl-N⁵-benzyloxy-L-ornithin-tert-butylester