2,6-Bis(((benzyloxy)carbonyl)amino)hexanoic acid

Base Information

• Chemical Name: 2,6-Bis(((benzyloxy)carbonyl)amino)hexanoic acid
• CAS No.: 55592-85-3
• Molecular Formula: C22H26N2O6
• Molecular Weight: 414.458
• European Community (EC) Number: 206-971-9
• NSC Number: 88474
• DSSTox Substance ID: DTXSID00275938
• Mol file: 55592-85-3.mol

Synonyms:55592-85-3;Z-DL-Lys(Z)-OH;2,6-Bis(((benzyloxy)carbonyl)amino)hexanoic acid;Z-D-Lys(Z)-OH;2,6-bis(phenylmethoxycarbonylamino)hexanoic acid;N-Alpha,epsilon-bis-Z-DL-lysine;DL-Lysine, N2,N6-bis[(phenylmethoxy)carbonyl]-;C22H26N2O6;N2,N6-Dibenzyloxycarbonyl-L-lysine;EINECS 206-971-9;NSC88474;N2,N6-Bis((benzyloxy)carbonyl)-L-lysine;2,6-bis(benzyloxycarbonylamino)hexanoic acid;(2R)-2,6-bis(phenylmethoxycarbonylamino)hexanoic acid;N2,N6-Bis-Cbz-DL-lysine;SCHEMBL806151;DTXSID00275938;MFCD00069644;NSC 88474;NSC-88474;DS-5095;CS-0149806;FT-0629773;FT-0641250;FT-0707524;Z-DL-Lys(Z)-OH, >=98.0% (TLC);F10934;2,6-Bis(((benzyloxy)carbonyl)amino)hexanoicacid;A825159;Nalpha,Nepsilon-Di-Z-DL-lysine, Nalpha,Nepsilon-di-Z-DL-lysine;2,6-Bis(((benZyloxy)carbonyl)amino)hexanoic acid (CbZ-DL-Lys(CbZ)-OH)

Chemical Property of 2,6-Bis(((benzyloxy)carbonyl)amino)hexanoic acid

Chemical Property:

• Vapor Pressure: 2.9E-18mmHg at 25°C
• Melting Point: 90-95 °C(lit.)
• Refractive Index: 1.568
• Boiling Point: 659 °C at 760 mmHg
• Flash Point: 352.4 °C
• PSA: 113.96000
• Density: 1.238 g/cm³
• LogP: 4.24450
• Storage Temp.: Store at 0-5°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 414.17908655
• Heavy Atom Count: 30
• Complexity: 530

Purity/Quality:

98%,99%, ^*data from raw suppliers

Z-DL-LYS(Z)-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NCCCCC(C(=O)O)NC(=O)OCC2=CC=CC=C2

Technology Process of 2,6-Bis(((benzyloxy)carbonyl)amino)hexanoic acid

There total 7 articles about 2,6-Bis(((benzyloxy)carbonyl)amino)hexanoic acid 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: 72.0%

N-ε-benzyloxycarbonyl lysine (32302-83-3,57705-97-2,67178-46-5,25931-47-9) + benzyl chloroformate (501-53-1,94274-21-2) → DL-N,N-di-CBZ-lysine (55592-85-3)

Guidance literature:

With sodium hydroxide; In toluene; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.ejmech.2014.07.063

Reference yield:

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + D-lysine (923-27-3,3506-25-0) → Nα,Nε-Bis(benzyloxycarbonyl)-D-lysine (405-39-0,55592-85-3,69677-02-7)

Guidance literature:

With sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1002/anie.201407944

Reference yield:

C43H37ClN4NiO3 → Nα,Nε-Bis(benzyloxycarbonyl)-D-lysine (405-39-0,55592-85-3,69677-02-7)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / methanol; water / 4 h / 40 °C

2: sodium hydrogencarbonate; sodium carbonate / tetrahydrofuran; water / 2 h / 20 °C

With hydrogenchloride; sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; methanol; water;

DOI:10.1002/anie.201407944

upstream raw materials:

2,6-diaminocaproic acid

benzyl chloroformate

N-ε-benzyloxycarbonyl lysine

D-lysine

Downstream raw materials:

N,N'-Dibenzyloxycarbonyl-(R)-β-homolysinmethylester

N-(N²,N⁶-bis-benzyloxycarbonyl-DL-lysyl)-glycine ethyl ester

(Z)-D-Lys(Z)-OPcp

(R)-{5-benzyloxycarbonylamino-1-[4-(4-ethyl-6-methoxy-5-pentyloxy-8-quinolylamino)pentylcarbamoyl]pentyl}carbamic acid benzyl ester

Refernces

• 1、 Schweiker, Stephanie S.,Loughlin, Wendy A.,Lohning, Anna S.,Petersson, Maria J.,Jenkins, Ian D.. "Synthesis, screening and docking of small heterocycles as Glycogen Phosphorylase inhibitors". . p. 584 - 594. Retrieved 2015/03/14.
• 2、 Tsunematsu, Hideaki,Isobe, Ryuichi,Mizusaki, Koichi,Makisumi, Satoru,Yamamoto, Magobei. "Differentiation Among the Four Diastereomers of Benzyloxycarbonyl-protected γ-Hydroxyornithine in Negative-ion Fast Atom Bombardment Mass Spectrometry". . p. 260 - 265. Retrieved 2007/10/02.