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

Base Information

• Chemical Name: N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-N^ε-(tert-butoxycarbonyl)-D-lysine methyl ester
• CAS No.: 130581-88-3
• Molecular Formula: C₂₈H₄₄N₄O₉
• Molecular Weight: 580.679

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

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

Chemical Property:

Purity/Quality:

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

There total 2 articles about N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-N^ε-(tert-butoxycarbonyl)-D-lysine 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: 85.0%

N-[(benzyloxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine (16947-84-5,62234-36-0) + (R)-2-amino-6-tert-butoxycarbonylaminohexanoic acid methyl ester (63328-49-4,1372256-52-4) → Nα-(benzyloxycarbonyl)-Nβ-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-Nε-(tert-butoxycarbonyl)-D-lysine methyl ester (130581-88-3)

Guidance literature:

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

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-Nε-(tert-butoxycarbonyl)-D-lysine methyl ester (130581-88-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 85 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (WSC*HCl) / CH₂Cl₂ / 2.5 h / Ambient temperature

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

DOI:10.1021/ja00029a031

Reference yield:

Nα-(benzyloxycarbonyl)-Nβ-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-Nε-(tert-butoxycarbonyl)-D-lysine methyl ester (130581-88-3) → N-(benzyloxycarbonyl)-D-alanyl-Nβ-(tert-butoxycarbonyl)-L-α,β-diaminopropionyl-Nε-(tert-butoxycarbonyl)-D-lysine methyl ester (138093-84-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / methanol / 17 h / 760 Torr / Ambient temperature

2: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (WSC*HCl) / CH₂Cl₂ / 1.5 h / Ambient temperature

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

DOI:10.1021/ja00029a031

upstream raw materials:

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

(R)-2-amino-6-tert-butoxycarbonylaminohexanoic acid methyl ester

(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^ε-(tert-butoxycarbonyl)-D-lysine methyl ester

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