Nalpha-Boc-Nalpha,delta,delta-tris(3-Boc-aminopropyl)-L-ornithine

Base Information

• Chemical Name: Nalpha-Boc-Nalpha,delta,delta-tris(3-Boc-aminopropyl)-L-ornithine
• CAS No.: 464926-00-9
• Molecular Formula: C34H65 N5 O10
• Molecular Weight: 703.91
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID40373189
• Wikidata: Q82161352
• Mol file: 464926-00-9.mol

Synonyms:464926-00-9;Nalpha-Boc-Nalpha,delta,delta-tris(3-Boc-aminopropyl)-L-ornithine;(2S)-5-[bis[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]-2-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]pentanoic acid;DTXSID40373189;MFCD06656443;AKOS027250946;N-alpha-Boc-N-alpha-N-delta-N-delta-tris(3-boc-aminopropyl)-L-ornithine;2,6,11,15-Tetraazahexadecanedioicacid,7-carboxy-6-[(1,1-dimethylethoxy)carbonyl]-11-[3-[[(1,1-dimethylethoxy)carbonyl]amino]propyl]-,1,16-bis(1,1-dimethylethyl)ester,(7S)-

Chemical Property of Nalpha-Boc-Nalpha,delta,delta-tris(3-Boc-aminopropyl)-L-ornithine

Chemical Property:

• PSA: 185.07000
• LogP: 6.67600
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 26
• Exact Mass: 703.47314329
• Heavy Atom Count: 49
• Complexity: 1010

Purity/Quality:

98%Min ^*data from raw suppliers

Nalpha-Boc-Nalpha,delta,delta-tris(3-Boc-aminopropyl)-L-ornithine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCCN(CCCC(C(=O)O)N(CCCNC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CCCNC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)NCCCN(CCC[C@@H](C(=O)O)N(CCCNC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CCCNC(=O)OC(C)(C)C

Technology Process of Nalpha-Boc-Nalpha,delta,delta-tris(3-Boc-aminopropyl)-L-ornithine

There total 3 articles about Nalpha-Boc-Nalpha,delta,delta-tris(3-Boc-aminopropyl)-L-ornithine 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: 89.0%

di-tert-butyl dicarbonate (24424-99-5) + Nα,Nδ,Nδ-tris(3-aminopropyl)ornithine (464925-99-3) → Nα-tert-butylcarbamoyl-Nα,Nδ,Nδ-tris(3-[tert-butylcarbamoylamino]propyl)ornithine (464926-00-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 6h;

DOI:10.1021/jm020233w

Reference yield:

L-ornithine hydrochloride (3184-13-2,36630-89-4) → Nα-tert-butylcarbamoyl-Nα,Nδ,Nδ-tris(3-[tert-butylcarbamoylamino]propyl)ornithine (464926-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / NaOH / methanol / 24 h / 20 °C

2: 100 percent Spectr_. / NaOH; H₂ / Raney nickel / aq. ethanol; H₂O / 16 h / 20 °C / 3102.89 Torr

3: 89 percent / 4 M NaOH / tetrahydrofuran; H₂O / 6 h / 20 °C

With sodium hydroxide; hydrogen; nickel; In tetrahydrofuran; methanol; ethanol; water; 1: Michael addition;

DOI:10.1021/jm020233w

Reference yield:

Nα,Nδ,Nδ-tris(2-cyanoethyl)ornithine hydrochloride → Nα-tert-butylcarbamoyl-Nα,Nδ,Nδ-tris(3-[tert-butylcarbamoylamino]propyl)ornithine (464926-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent Spectr_. / NaOH; H₂ / Raney nickel / aq. ethanol; H₂O / 16 h / 20 °C / 3102.89 Torr

2: 89 percent / 4 M NaOH / tetrahydrofuran; H₂O / 6 h / 20 °C

With sodium hydroxide; hydrogen; nickel; In tetrahydrofuran; ethanol; water;

DOI:10.1021/jm020233w

upstream raw materials:

di-tert-butyl dicarbonate

Nα,Nδ,Nδ-tris(3-aminopropyl)ornithine

L-ornithine hydrochloride

Downstream raw materials:

N₁-[2-((1S)-1-[tert-butylcarbamoylamino(3-[tert-butylcarbamoylamino]propyl)amino]-4-[di(3-[tert-butylcarbamoylamino]propyl)amino]butylcarboxamido)ethyl]-3,4-di[oleyloxy]benzamide

{4-[bis-(3-tert-butoxycarbonylamino-propyl)amino]-(S)-1-[2-(2-{(3,4-di(oleyloxy)benzoyl)amino}-ethyldisulfanyl)-ethylcarbamoyl]-butyl}-(3-tert-butoxycarbonylaminopropyl)-carbamic acid tert-butyl ester