Z-Orn(Z)-OH

Base Information

• Chemical Name: Z-Orn(Z)-OH
• CAS No.: 2274-58-0
• Molecular Formula: C21H24N2O6
• Molecular Weight: 400.431
• Hs Code.: 2924299090
• European Community (EC) Number: 218-889-0
• DSSTox Substance ID: DTXSID10945413
• ChEMBL ID: CHEMBL1560422
• Mol file: 2274-58-0.mol

Synonyms:Z-Orn(Z)-OH;(2S)-2,5-bis(phenylmethoxycarbonylamino)pentanoic acid;2,5-Bis-benzyloxycarbonylamino-pentanoic acid;N~2~,N~5~-bis[(benzyloxy)carbonyl]ornithine;2,5-bis(phenylmethoxycarbonylamino)pentanoic acid;MLS001207543;SCHEMBL4173693;CHEMBL1560422;DTXSID10945413;HMS2830F14;N-alpha,N-delta-di-Z-L-ornithine;EINECS 218-889-0;MFCD00339525;STK368896;AKOS000666662;AKOS016401669;N2,N5-Dibenzyloxycarbonyl-L-ornithine;N2,N5-bis[(benzyloxy)carbonyl]ornithine;NCGC00245011-01;LS-08320;SMR000504906;FT-0629771;N,N'-Bis[(phenylmethoxy)carbonyl]-L-ornithine;AB00812873-06;2,5-Bis(((benzyloxy)carbonyl)amino)pentanoic acid;SR-01000310191;SR-01000310191-1;2,5-DI{[(BENZYLOXY)CARBONYL]AMINO}PENTANOIC ACID;N~2~,N~5~-Bis[(benzyloxy)(hydroxy)methylidene]ornithine;39897-05-7

Chemical Property of Z-Orn(Z)-OH

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 302oC
• Boiling Point: 653.3 °C at 760 mmHg
• PKA: 3.94±0.21(Predicted)
• Flash Point: 348.9 °C
• PSA: 113.96000
• Density: 1.259 g/cm³
• LogP: 3.85440
• Storage Temp.: Store at RT.
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 400.16343649
• Heavy Atom Count: 29
• Complexity: 515

Purity/Quality:

99% ^*data from raw suppliers

(S)-2,5-Bis(((benzyloxy)carbonyl)-amino)pentanoic acid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Z-Orn(Z)-OH

There total 4 articles about Z-Orn(Z)-OH 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: 92.0%

L-ornithine hydrochloride (3184-13-2,36630-89-4) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-2,5-bis-(benzyloxycarbonylamino)pentanoic acid (2274-58-0)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo302181k

Reference yield: 78.0%

D-ornithine hydrochloride (16682-12-5,36630-89-4) + benzyl chloroformate (501-53-1,94274-21-2) → N,N'-di(benzyloxycarbonyl)-D-ornithine (2274-58-0,39897-05-7,13594-49-5)

Guidance literature:

With sodium hydroxide; at 0 ℃; for 1h;

Reference yield:

L-ornithine (70-26-8,25104-12-5,410523-47-6) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-2,5-bis-(benzyloxycarbonylamino)pentanoic acid (2274-58-0)

Guidance literature:

With sodium hydroxide; at 0 ℃;

upstream raw materials:

L-ornithine

benzyl chloroformate

L-ornithine hydrochloride

D-ornithine

Downstream raw materials:

N,N'-Bis-(N,N'-di-benzyloxycarbonyl-L-ornithyl)-hexamethylendiamin

N-taurine

N^ε-(benzyloxycarbonyl)ornithine N-carboxyanhydride

N-(N²,N⁵-bis-benzyloxycarbonyl-L-ornithyl)-glycine ethyl ester

Refernces

• 1、 -. "CONJUGATES COMPRISING PEPTIDE GROUPS AND METHODS RELATED THERETO". Page/Page column 144; 145. . Retrieved 2017/08/08.
• 2、 Yang, Jianxin,Zhao, Kang,Gong, Youxiang,Vologodskii, Alexander,Kallenbach, Neville R.. "α-Helix nucleation constant in copolypeptides of alanine and ornithine or lysine". . p. 10646 - 10652. Retrieved 2007/10/03.