(S)-5-Benzyloxyamino-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester

Base Information

• Chemical Name: (S)-5-Benzyloxyamino-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester
• CAS No.: 90195-03-2
• Molecular Formula: C₂₁H₃₄N₂O₅
• Molecular Weight: 394.511
• Mol file: 90195-03-2.mol

Synonyms:(S)-5-Benzyloxyamino-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester

Chemical Property of (S)-5-Benzyloxyamino-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-Benzyloxyamino-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester

There total 4 articles about (S)-5-Benzyloxyamino-2-tert-butoxycarbonylamino-pentanoic acid 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:

N-<(2,2,2-trichloroethoxy)carbonyl>-O-benzylhydroxylamine (90195-00-9) → (S)-5-Benzyloxyamino-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester (90195-03-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / PPh₃, DEAD / tetrahydrofuran / 16 h / Ambient temperature

2: Zn dust, acetic acid / 1 h / Ambient temperature

With acetic acid; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/jo00187a023

Reference yield:

O-benzylhydoxylamine hydrochloride (2687-43-6) → (S)-5-Benzyloxyamino-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester (90195-03-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / pyridine / acetonitrile / 1 h / Ambient temperature

2: 80 percent / PPh₃, DEAD / tetrahydrofuran / 16 h / Ambient temperature

3: Zn dust, acetic acid / 1 h / Ambient temperature

With pyridine; acetic acid; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo00187a023

Reference yield:

N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2) → (S)-5-Benzyloxyamino-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester (90195-03-2)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 80 percent / PPh₃, DEAD / tetrahydrofuran / 16 h / Ambient temperature

3: Zn dust, acetic acid / 1 h / Ambient temperature

With sodium tetrahydroborate; acetic acid; triethylamine; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/jo00187a023

upstream raw materials:

N-<(2,2,2-trichloroethoxy)carbonyl>-O-benzylhydroxylamine

O-benzylhydoxylamine hydrochloride

N-tert-butoxycarbonyl glutamic acid tert-butyl ester

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

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