6'-N-[N^α-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-N^ε-(benzyloxycarbonyl)-L-lysyl]neamine

Base Information

• Chemical Name: 6'-N-[N^α-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-N^ε-(benzyloxycarbonyl)-L-lysyl]neamine
• CAS No.: 886208-75-9
• Molecular Formula: C₄₀H₅₅N₉O₁₃
• Molecular Weight: 869.929

Synonyms:6'-N-[N^α-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-N^ε-(benzyloxycarbonyl)-L-lysyl]neamine

Chemical Property of 6'-N-[N^α-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-N^ε-(benzyloxycarbonyl)-L-lysyl]neamine

Chemical Property:

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Technology Process of 6'-N-[N^α-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-N^ε-(benzyloxycarbonyl)-L-lysyl]neamine

There total 4 articles about 6'-N-[N^α-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-N^ε-(benzyloxycarbonyl)-L-lysyl]neamine 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: 27.4%

Nα-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-Nε-(benzyloxycarbonyl)-L-lysine (886208-40-8) + neomycin A (3947-65-7) → 6'-N-[Nα-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-Nε-(benzyloxycarbonyl)-L-lysyl]neamine (886208-75-9) + 6'-N-[Nα-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-Nε-(benzyloxycarbonyl)-D-lysyl]neamine (886208-74-8)

Guidance literature:

N^α-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-N^ε-(benzyloxycarbonyl)-L-lysine; With WSC*HCl; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

neomycin A; In water; N,N-dimethyl-formamide; at 0 - 20 ℃; for 26h;

DOI:10.1016/j.bmc.2005.11.056

Reference yield:

tert-butyl Nα-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-Nε-(benzyloxycarbonyl)-L-lysinate (886208-39-5) → 6'-N-[Nα-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-Nε-(benzyloxycarbonyl)-L-lysyl]neamine (886208-75-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TFA / CH₂Cl₂ / 3.5 h

2.1: WSC*HCl / dimethylformamide / 0.5 h / 0 °C

2.2: 27.4 percent / dimethylformamide; H₂O / 26 h / 0 - 20 °C

With WSC*HCl; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.11.056

Reference yield:

N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride (5978-22-3,1426213-63-9) → 6'-N-[Nα-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-Nε-(benzyloxycarbonyl)-L-lysyl]neamine (886208-75-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 72.4 percent / PyBrop; DIEA / dimethylformamide / 23 h / 0 - 20 °C

2.1: TFA / CH₂Cl₂ / 3.5 h

3.1: WSC*HCl / dimethylformamide / 0.5 h / 0 °C

3.2: 27.4 percent / dimethylformamide; H₂O / 26 h / 0 - 20 °C

With WSC*HCl; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.11.056

upstream raw materials:

N^α-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-N^ε-(benzyloxycarbonyl)-L-lysine

neomycin A

tert-butyl N^α-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-N^ε-(benzyloxycarbonyl)-L-lysinate

N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride

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