N_α-(9-fluorenylmethoxycarbonyl)-N_ε-(2-nitrobenzyloxycarbonyl)-lysine

Base Information

• Chemical Name: N_α-(9-fluorenylmethoxycarbonyl)-N_ε-(2-nitrobenzyloxycarbonyl)-lysine
• CAS No.: 174653-61-3
• Molecular Formula: C₂₉H₂₉N₃O₈
• Molecular Weight: 547.565
• Mol file: 174653-61-3.mol

Synonyms:N_α-(9-fluorenylmethoxycarbonyl)-N_ε-(2-nitrobenzyloxycarbonyl)-lysine

Chemical Property of N_α-(9-fluorenylmethoxycarbonyl)-N_ε-(2-nitrobenzyloxycarbonyl)-lysine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N_α-(9-fluorenylmethoxycarbonyl)-N_ε-(2-nitrobenzyloxycarbonyl)-lysine

There total 7 articles about N_α-(9-fluorenylmethoxycarbonyl)-N_ε-(2-nitrobenzyloxycarbonyl)-lysine 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: 68.0%

Fmoc-Lys-OH (105047-45-8) + 4-nitrobenzyl chloroformate (4457-32-3) → Nα-(9-fluorenylmethoxycarbonyl)-Nε-(2-nitrobenzyloxycarbonyl)-lysine (174653-61-3)

Guidance literature:

4-nitrobenzyl chloroformate; With sodium azide; In 1,4-dioxane; water; for 1h;

Fmoc-Lys-OH; With sodium carbonate; In 1,4-dioxane; for 16h; pH=9;

DOI:10.1002/chem.201803899

Reference yield: 42.0%

4-nitrobenzyl carbonazidate (71731-66-3) + Fmoc-Lys-OH (105047-45-8) → Nα-(9-fluorenylmethoxycarbonyl)-Nε-(2-nitrobenzyloxycarbonyl)-lysine (174653-61-3)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; for 24h;

DOI:10.1002/ejoc.201402111

Reference yield:

Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) → Nα-(9-fluorenylmethoxycarbonyl)-Nε-(2-nitrobenzyloxycarbonyl)-lysine (174653-61-3)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

2: sodium carbonate / 1,4-dioxane; water / 24 h

With sodium carbonate; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water;

DOI:10.1002/ejoc.201402111

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

o-nitrobenzyl chloroformate

2-Nitrobenzyl alcohol

4-nitrobenzyl carbonazidate

Downstream raw materials:

H-Tyr-D-Ala-Phe-Glu(<*>)-Val-Val-Lys(<*>)-NH₂

c[Lys-Lys(CO-Tr-Bn)-Leu-Lys-Lys-(p-nitrobenzyloxycarbonyl)-Phe-Lys-Lys-Leu-Gln]

c[Lys-Lys(CO-CCH)-Leu-Lys-Lys(hexanoic acid)-Phe-Lys-Lys-Leu-Gln]

c[Lys-Lys(1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl)-Leu-Lys-Lys(CO-C₅H₁₁)-Phe-Lys-Lys-Leu-Gln]