N⁵-Acetyl-N⁵-benzyloxy-L-ornithin

Base Information

• Chemical Name: N⁵-Acetyl-N⁵-benzyloxy-L-ornithin
• CAS No.: 52816-28-1
• Molecular Formula: C₁₄H₂₀N₂O₄
• Molecular Weight: 280.324
• Mol file: 52816-28-1.mol

Synonyms:N⁵-Acetyl-N⁵-benzyloxy-L-ornithin

Chemical Property of N⁵-Acetyl-N⁵-benzyloxy-L-ornithin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N⁵-Acetyl-N⁵-benzyloxy-L-ornithin

There total 24 articles about N⁵-Acetyl-N⁵-benzyloxy-L-ornithin 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: 76.0%

N5-Acetyl-N5-benzyloxy-L-ornithin-tert-butylester (92412-95-8) → N5-Acetyl-N5-benzyloxy-L-ornithin (52816-28-1)

Guidance literature:

With trifluoroacetic acid; at 0 ℃; for 8h;

DOI:10.1002/jlac.198419840804

Reference yield: 57.0%

L-N(2)-Boc-N(5)-acetyl-N(5)-benzyloxyornithine tert-butyl ester (90195-02-1) → N5-Acetyl-N5-benzyloxy-L-ornithin (52816-28-1)

Guidance literature:

With trifluoroacetic acid; for 1h; Ambient temperature;

DOI:10.1021/jo00187a023

Reference yield:

N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2) → N5-Acetyl-N5-benzyloxy-L-ornithin (52816-28-1)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jo00187a023

upstream raw materials:

N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithine

L-N⁽²⁾-Boc-N⁽⁵⁾-acetyl-N⁽⁵⁾-benzyloxyornithine tert-butyl ester

N⁵-Acetyl-N⁵-benzyloxy-L-ornithin-tert-butylester

2-Acetylamino-5-(acetyl-benzyloxy-amino)-pentanoic acid

Downstream raw materials:

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

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

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

methyl(S)-5-[N-(benzyloxy)acetamido]-2-{(S)-5-[N-(benzyloxy)acetamido]-2-[(tert-butoxy-carbonyl)amino]pentanamide}pentanoate