N2,N2-Bis[2-(1,1-diMethylethoxy)-2-oxoethyl]-N6-[(phenylMethoxy)carbonyl]-L-lysine 1,1-DiMethylethyl Ester

Base Information

• Chemical Name: N2,N2-Bis[2-(1,1-diMethylethoxy)-2-oxoethyl]-N6-[(phenylMethoxy)carbonyl]-L-lysine 1,1-DiMethylethyl Ester
• CAS No.: 205379-07-3
• Molecular Formula: C30H48N2O8
• Molecular Weight: 564.72
• Mol file: 205379-07-3.mol

Synonyms:(5S)-N-Benzyloxycarbonyl-N-(5-AMino-1-carboxypentyl)iMinodiacetic Acid, Tri-t-butyl Ester;N2,N2-Bis[2-(1,1-diMethylethoxy)-2-oxoethyl]-N6-[(phenylMethoxy)carbonyl]-L-lysine 1,1-DiMethylethyl Ester

Chemical Property of N2,N2-Bis[2-(1,1-diMethylethoxy)-2-oxoethyl]-N6-[(phenylMethoxy)carbonyl]-L-lysine 1,1-DiMethylethyl Ester

Chemical Property:

• PSA: 123.96000
• LogP: 4.98320
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Hexane

Purity/Quality:

(5S)-N-Benzyloxycarbonyl-N-(5-Amino-1-carboxypentyl)iminodiaceticAcid,Tri-t-butylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A protected chelating agent.

Technology Process of N2,N2-Bis[2-(1,1-diMethylethoxy)-2-oxoethyl]-N6-[(phenylMethoxy)carbonyl]-L-lysine 1,1-DiMethylethyl Ester

There total 5 articles about N2,N2-Bis[2-(1,1-diMethylethoxy)-2-oxoethyl]-N6-[(phenylMethoxy)carbonyl]-L-lysine 1,1-DiMethylethyl 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: 100.0%

bromoacetic acid tert-butyl ester (5292-43-3) + N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride (5978-22-3,1426213-63-9) → Nα,Nα-bis[(tert-butyloxycarbonyl)methyl]-Nε-benzyloxycarbonyl-L-lysine tert-butyl ester (205379-07-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 55 ℃; Inert atmosphere;

DOI:10.1021/ja505695w

Reference yield: 100.0%

bromoacetic acid tert-butyl ester (5292-43-3) + Nε-benzyloxycarbonyl-L-lysine tert-butyl ester (63628-63-7) → Nα,Nα-bis[(tert-butyloxycarbonyl)methyl]-Nε-benzyloxycarbonyl-L-lysine tert-butyl ester (205379-07-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 65 ℃; for 18h;

DOI:10.1246/bcsj.20190034

Reference yield:

Boc-Lys(Z)-OH (2389-45-9) → Nα,Nα-bis[(tert-butyloxycarbonyl)methyl]-Nε-benzyloxycarbonyl-L-lysine tert-butyl ester (205379-07-3)

Guidance literature:

Multi-step reaction with 3 steps

1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 1.5 h / 20 °C

2: hydrogenchloride / ethyl acetate

3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 65 °C

With hydrogenchloride; dmap; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.20190034

upstream raw materials:

bromoacetic acid tert-butyl ester

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

Nε-benzyloxycarbonyl-L-lysine tert-butyl ester

Boc-Lys(Z)-OH

Downstream raw materials:

C₃₁H₂₉N₃O₁₁S

N_α,N_α-bis(carboxymethyl)-N_ε-(benzyloxycarbonyl)-L-lysine

TO-bis NTA

N,N-bis(carboxymethyl)-L-lysine

Refernces

• 1、 June, Ronald K.,Gogoi, Khirud,Eguchi, Akiko,Cui, Xian-Shu,Dowdy, Steven F.. "Synthesis of a pH-sensitive nitrilotriacetic linker to peptide transduction domains to enable intracellular delivery of histidine imidazole ring-containing macromolecules". . p. 10680 - 10682. Retrieved 2010.
• 2、 Cabanas-Dans, Jordi,Rodrigues, Emilie Dooms,Landman, Ellie,Van Weerd, Jasper,Van Blitterswijk, Clemens,Verrips, Theo,Huskens, Jurriaan,Karperien, Marcel,Jonkheijm, Pascal. "A supramolecular host-guest carrier system for growth factors employing VHH fragments". . p. 12675 - 12681. Retrieved 2014.
• 3、 Tinazli, Ali,Tang, Juin,Valiokas, Ramunas,Picuric, Srdjan,Lata, Suman,Piehler, Jacob,Liedberg, Bo,Tampe, Robert. "High-affinity chelator thiols for switchable and oriented immobilization of histidine-tagged proteins: A generic platform for protein chip technologies". . p. 5249 - 5259. Retrieved 2005.
• 4、 -. "Grid coatings for capture of proteins and other compounds". Page/Page column 19-21. . Retrieved 2021/04/28.
• 5、 Gatterdam, Karl,Joest, Eike F.,Gatterdam, Volker,Tampé, Robert. "The Scaffold Design of Trivalent Chelator Heads Dictates Affinity and Stability for Labeling His-tagged Proteins in vitro and in Cells". supporting information. p. 12395 - 12399. Retrieved 2018/09/18.