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

Base Information

• Chemical Name: L-N⁽²⁾-Boc-N⁽⁵⁾-Cbz-N⁽⁵⁾-benzyloxyornithine tert-butyl ester
• CAS No.: 90219-04-8
• Molecular Formula: C₂₉H₄₀N₂O₇
• Molecular Weight: 528.646
• Mol file: 90219-04-8.mol

Synonyms:L-N⁽²⁾-Boc-N⁽⁵⁾-Cbz-N⁽⁵⁾-benzyloxyornithine tert-butyl ester

Chemical Property of L-N⁽²⁾-Boc-N⁽⁵⁾-Cbz-N⁽⁵⁾-benzyloxyornithine tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-N⁽²⁾-Boc-N⁽⁵⁾-Cbz-N⁽⁵⁾-benzyloxyornithine tert-butyl ester

There total 2 articles about L-N⁽²⁾-Boc-N⁽⁵⁾-Cbz-N⁽⁵⁾-benzyloxyornithine tert-butyl 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: 66.0%

N-benzyloxycarbonyl-O-benzylhydroxylamine (15255-86-4) + tert-butyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanoate (90194-99-3) → L-N(2)-Boc-N(5)-Cbz-N(5)-benzyloxyornithine tert-butyl ester (90219-04-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 5h; Ambient temperature;

DOI:10.1021/jo00187a023

Reference yield:

N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2) → L-N(2)-Boc-N(5)-Cbz-N(5)-benzyloxyornithine tert-butyl ester (90219-04-8)

Guidance literature:

Multi-step reaction with 2 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

With sodium tetrahydroborate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/jo00187a023

Reference yield: 55.0%

acetic anhydride (108-24-7) + L-N(2)-Boc-N(5)-Cbz-N(5)-benzyloxyornithine tert-butyl ester (90219-04-8) → L-N(2)-Boc-N(5)-acetyl-N(5)-benzyloxyornithine tert-butyl ester (90195-02-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; under 760 Torr; 1.) 1.5 h, 0 deg C, 2.) 2.5 h, room temperature;

DOI:10.1021/jo00187a023

upstream raw materials:

N-benzyloxycarbonyl-O-benzylhydroxylamine

tert-butyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanoate

N-tert-butoxycarbonyl glutamic acid tert-butyl ester

Downstream raw materials:

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

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

N-Benzyloxy-N-[3-((S)-2,5-dioxo-oxazolidin-4-yl)-propyl]-acetamide

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