N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-N^δ-(tert-butoxycarbonyl)-D-ornithine methyl ester

Base Information

• Chemical Name: N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-N^δ-(tert-butoxycarbonyl)-D-ornithine methyl ester
• CAS No.: 130619-14-6
• Molecular Formula: C₂₇H₄₂N₄O₉
• Molecular Weight: 566.652

Synonyms:N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-N^δ-(tert-butoxycarbonyl)-D-ornithine methyl ester

Chemical Property of N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-N^δ-(tert-butoxycarbonyl)-D-ornithine methyl ester

Chemical Property:

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Technology Process of N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-N^δ-(tert-butoxycarbonyl)-D-ornithine methyl ester

There total 3 articles about N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-N^δ-(tert-butoxycarbonyl)-D-ornithine methyl 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: 82.0%

methyl (R)-2-amino-5-[(tert-butoxycarbonyl)amino]pentanoate (51186-41-5) + N-[(benzyloxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine (16947-84-5,62234-36-0) → Nα-(benzyloxycarbonyl)-Nβ-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-Nδ-(tert-butoxycarbonyl)-D-ornithine methyl ester (130619-14-6)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 2.5h; Ambient temperature;

DOI:10.1021/ja00029a031

Reference yield:

(R)-methyl 2-(benzyloxycarbonylamino)-5-(tert-butoxycarbonylamino)pentanoate (130581-87-2) → Nα-(benzyloxycarbonyl)-Nβ-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-Nδ-(tert-butoxycarbonyl)-D-ornithine methyl ester (130619-14-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pt/C / methanol / 14 h / 760 Torr / Ambient temperature

2: 82 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (WSC) / CH₂Cl₂ / 2.5 h / Ambient temperature

With hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; platinum on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja00029a031

Reference yield:

(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid (35761-26-3) → Nα-(benzyloxycarbonyl)-Nβ-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-Nδ-(tert-butoxycarbonyl)-D-ornithine methyl ester (130619-14-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / tetrahydrofuran; H₂O / 5 h / Ambient temperature

2: 82 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (WSC) / CH₂Cl₂ / 2.5 h / Ambient temperature

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja00029a031

upstream raw materials:

methyl (R)-2-amino-5-[(tert-butoxycarbonyl)amino]pentanoate

N-[(benzyloxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine

(R)-methyl 2-(benzyloxycarbonylamino)-5-(tert-butoxycarbonylamino)pentanoate

(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid

Downstream raw materials:

N-(benzyloxycarbonyl)-D-alanyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-N^δ-(tert-butoxycarbonyl)-D-ornithine methyl ester

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