Z-ORN(BOC)-OH

Base Information

• Chemical Name: Z-ORN(BOC)-OH
• CAS No.: 7733-29-1
• Molecular Formula: C18H26N2O6
• Molecular Weight: 366.414
• Hs Code.: 2924299090
• Mol file: 7733-29-1.mol

Synonyms:Ornithine,N2,N5-dicarboxy-, N2-benzyl N5-tert-butyl ester, L- (7CI,8CI);(2S)-5-((tert-Butoxycarbonyl)amino)-2-((benzyloxycarbonyl)amino)pentanoicacid;N-a-Benzyloxycarbonyl-N-d-tert-butoxycarbonyl-L-ornithine;NSC 336232;

Chemical Property of Z-ORN(BOC)-OH

Chemical Property:

• Appearance/Colour: white - off-white powder
• Vapor Pressure: 2.99E-14mmHg at 25°C
• Melting Point: 96-103ºC
• Refractive Index: 1.526
• Boiling Point: 579.1 °C at 760 mmHg
• PKA: 3.94±0.21(Predicted)
• Flash Point: 304 °C
• PSA: 113.96000
• Density: 1.193 g/cm³
• LogP: 3.45270
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

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

Z-L-Orn(Boc)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Z-ORN(BOC)-OH

There total 13 articles about Z-ORN(BOC)-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: 95.0%

benzyl chloroformate (501-53-1,94274-21-2) + copper(II) complex of Nδ-tert-butoxycarbonyl-L-ornithine → Z-Orn(Boc)-OH (7733-29-1,199924-46-4)

Guidance literature:

copper(II) complex of N^δ-tert-butoxycarbonyl-L-ornithine; With 8-quinolinol; sodium carbonate; In acetone; for 1h;

benzyl chloroformate; With 1-hydroxy-pyrrolidine-2,5-dione; In water; at -5 ℃; for 0.5h;

DOI:10.1248/cpb.49.1189

Reference yield: 90.0%

Nδ-(tert-butoxycarbonyl)-L-ornithine (13650-49-2,184576-63-4) + benzyl chloroformate (501-53-1,94274-21-2) → Z-Orn(Boc)-OH (7733-29-1,199924-46-4)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 ℃; for 12h;

DOI:10.1016/j.ejmech.2018.02.053

Reference yield: 82.0%

benzyl-8-quinolyl carbonate (19506-72-0) + di-tert-butyl dicarbonate (24424-99-5) + L-ornithine hydrochloride (3184-13-2,36630-89-4) → Z-Orn(Boc)-OH (7733-29-1,199924-46-4)

Guidance literature:

Multistep reaction;

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

Nα-benzyloxycarbonyl-L-ornithine

1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate

(2S)-2-{[(benzyloxy)carbonyl]amino}-4-(dimethylamino)butanoic acid

Downstream raw materials:

N^α-Benzyloxycarbonyl-N^δ-tert.butoxycarbonyl-L-ornithin-p-nitrophenylester

Z-Orn(Boc)-Asp(OBzl)-NH₂

Z-Orn(Boc)-Asp(OBzl)-Phe-NH₂

Nα-Benzyloxycarbonyl-Nδ-tert-butyloxycarbonyl-L-ornithyl-Nδ-tert-butyloxycarbonyl-L-ornithinoctadecylamid

Refernces

• 1、 Harris, Austin P.,Phillips, Robert S.. "Benzimidazole analogs of l-tryptophan are substrates and inhibitors of tryptophan indole lyase from Escherichia coli". . p. 1807 - 1817. Retrieved 2013/06/05.
• 2、 Martin, Nathaniel I.,Beeson, William T.,Woodward, Joshua J.,Marletta, Michael A.. "NG-aminoguanidines from primary amines and the preparation of nitric oxide synthase inhibitors". . p. 924 - 931. Retrieved 2008/09/20.