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

Base Information

• Chemical Name: tert-butyl N^α-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-N^ε-(benzyloxycarbonyl)-L-lysinate
• CAS No.: 886208-39-5
• Molecular Formula: C₃₂H₃₉N₅O₈
• Molecular Weight: 621.69

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

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

Chemical Property:

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

There total 1 articles about tert-butyl N^α-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-N^ε-(benzyloxycarbonyl)-L-lysinate 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: 72.4%

N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride (5978-22-3,1426213-63-9) + [N4-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid (144564-95-4) → tert-butyl Nα-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-Nε-(benzyloxycarbonyl)-L-lysinate (886208-39-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 23h;

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-[(cytosin-1-yl)acetyl]-D-lysyl]neamine

Guidance literature:

Multi-step reaction with 3 steps

1.1: TFA / CH₂Cl₂ / 3.5 h

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

2.2: 16.2 percent / dimethylformamide; H₂O / 26 h / 0 - 20 °C

3.1: 74.7 percent / TFA; m-cresol; thioanisol / trimethylsilyl trifluoromethanesulfonate / 2.5 h / 0 - 20 °C

With methyl-phenyl-thioether; WSC*HCl; 3-methyl-phenol; trifluoroacetic acid; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; N,N-dimethyl-formamide;

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-[(cytosin-1-yl)acetyl]-L-lysyl]neamine

Guidance literature:

Multi-step reaction with 3 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

3.1: 73.8 percent / TFA; m-cresol; thioanisol / trimethylsilyl trifluoromethanesulfonate / 2.5 h / 0 - 20 °C

With methyl-phenyl-thioether; WSC*HCl; 3-methyl-phenol; trifluoroacetic acid; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.11.056

upstream raw materials:

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

[N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid

Downstream raw materials:

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

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

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

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