(S)-2-(((Benzyloxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoic acid

Base Information

• Chemical Name: (S)-2-(((Benzyloxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoic acid
• CAS No.: 199924-46-4
• Molecular Formula: C18H26N2O6
• Molecular Weight: 366.41
• DSSTox Substance ID: DTXSID90428557
• Nikkaji Number: J1.559.891C
• Wikidata: Q72470219
• Mol file: 199924-46-4.mol

Synonyms:Z-ORN(BOC)-OH;199924-46-4;7733-29-1;(S)-2-(((Benzyloxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoic acid;Cbz-Orn(Boc)-OH;Z-Ndelta-Boc-L-ornithine;C18H26N2O6;(2S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)pentanoic acid;Nalpha-Cbz-Ndelta-Boc-L-ornithine;NSC 336232;MFCD00038268;(2S)-2-[(benzyloxycarbonyl)amino]-5-((tert-butoxycarbonyl)amino]pentanoic acid;(2S)-2-[(benzyloxycarbonyl)amino]-5-[(tert-butoxycarbonyl)amino]pentanoic acid;ZOrn(Boc)OH;Z-L-Orn(Boc)-OH;Z--Orn(Boc)--OH;N5-Boc-N2-Cbz-L-ornithine;CS-WAA0071;SCHEMBL1021938;DTXSID90428557;RWQCKACYKKSOKK-AWEZNQCLSA-N;AC7943;AKOS015841467;Ornithine, N5-[(1,1-dimethylethoxy)carbonyl]-N2-[(phenylmethoxy)carbonyl]-;AS-71708;CS-0035382;A839054;J-012927;N-a-Benzyloxycarbonyl-N-d-tert-butoxycarbonyl-L-ornithine;N-alpha-Benzyloxycarbonyl-N-delta-t-butyloxycarbonyl-L-ornithine;N2-[(benzyloxy)carbonyl]-N5-(tert-butoxycarbonyl)-L-ornithine;N5-(tert-butoxycarbonyl)-N2-[(benzyloxy)carbonyl]-L-ornithine;(S)-N2-(benzyloxycarbonyl)-N5-(tert-butyloxycarbonyl)-ornithine;(S)-2-(benzyloxycarbonylamino)-5-(tert-butoxycarbonylamino)pentanoic acid;(2S)-2-{[(benzyloxy)carbonyl]amino}-5-{[(tert-butoxy)carbonyl]amino}pentanoic acid;(2S)-5-((tert-Butoxycarbonyl)amino)-2-((benzyloxycarbonyl)amino)pentanoic acid;(S)-2-(((Benzyloxy)carbonyl)amino)-5-((t-butoxycarbonyl)amino)pentanoic acid;(S)-2-(((Benzyloxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoicacid;N-alpha-BenZyloxycarbonyl-N-delta-t-butyloxycarbonyl-L-ornithine (CbZ-L-Orn(Boc)-OH)

Chemical Property of (S)-2-(((Benzyloxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoic acid

Chemical Property:

• Melting Point: 98-99
• Boiling Point: 579.1±50.0 °C(Predicted)
• PKA: 3.94±0.21(Predicted)
• PSA: 113.96000
• Density: 1.193±0.06 g/cm3(Predicted)
• LogP: 3.45270
• Storage Temp.: Store at RT.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 366.17908655
• Heavy Atom Count: 26
• Complexity: 469

Purity/Quality:

99.0% ^*data from raw suppliers

Z-Orn(Boc)-OH ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCCC(C(=O)O)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)NCCC[C@@H](C(=O)O)NC(=O)OCC1=CC=CC=C1

Technology Process of (S)-2-(((Benzyloxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoic acid

There total 14 articles about (S)-2-(((Benzyloxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoic 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + N-carbobenzyloxy-(D)-ornithine → (R)-Nα-Z-Nδ-Boc-ornithine (98264-52-9,199924-46-4)

Guidance literature:

With potassium carbonate; In 1,4-dioxane;

DOI:10.1016/S0960-894X(99)00628-9

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

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-ornithine methyl ester

Z-Orn(Boc)-β-Ala-OBzl

Nα-Benzyloxycarbonyl-Nδ-(Nα-benzyloxycarbonyl-Nδ-tert-butyloxycarbonyl-L-ornithyl)-L-ornithinoctadecylamid

3-<3-<2-α-benzyloxycarbonyl-N^δ-tert-butoxycarbonyl-(S)-ornithylamino>ethyl>-4-methoxyphenyl>-N-tert-butoxycarbonyl-O-methyl-(S)-tyrosinemethyl ester