N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester

Base Information

• Chemical Name: N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester
• CAS No.: 124620-52-6
• Molecular Formula: C₂₇H₃₃Cl₃N₂O₇
• Molecular Weight: 603.927

Synonyms:N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester

Chemical Property of N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester

There total 6 articles about N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-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: 71.0%

N-<(2,2,2-trichloroethoxy)carbonyl>-O-benzylhydroxylamine (90195-00-9) + (S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate (124620-51-5) → N2-(benzyloxycarbonyl)-N5-(benzyloxy)-N5-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester (124620-52-6)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jm00107a013

Reference yield:

(S)-2-Benzyloxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid tert-butyl ester → N2-(benzyloxycarbonyl)-N5-(benzyloxy)-N5-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester (124620-52-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium borohydride / tetrahydrofuran; H₂O / 4 h / Ambient temperature

2: 71 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / Ambient temperature

With sodium tetrahydroborate; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; water;

DOI:10.1021/jm00107a013

Reference yield:

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester (5891-45-2) → N2-(benzyloxycarbonyl)-N5-(benzyloxy)-N5-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester (124620-52-6)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / tetrahydrofuran / 1 h / 0 °C

2: sodium borohydride / tetrahydrofuran; H₂O / 4 h / Ambient temperature

3: 71 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / Ambient temperature

With sodium tetrahydroborate; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran; water;

DOI:10.1021/jm00107a013

upstream raw materials:

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

(S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate

N-benzyloxycarbonyl-L-glutamic acid

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester

Downstream raw materials:

N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithine 1-tert-butyl ester

(S)-5-Allyloxycarbonylamino-2-benzyloxycarbonylamino-pentanoic acid tert-butyl ester

N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(allyloxycarbonyl)-L-ornithine 1-tert-butyl ester

N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithine 1-methyl ester

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