Boc-orn(boc)-OH

Base Information

• Chemical Name: Boc-orn(boc)-OH
• CAS No.: 57133-29-6
• Molecular Formula: C15H28N2O6
• Molecular Weight: 332.397
• DSSTox Substance ID: DTXSID60426767
• Nikkaji Number: J590.442K
• Wikidata: Q72446893
• Mol file: 57133-29-6.mol

Synonyms:BOC-ORN(BOC)-OH;57133-29-6;(S)-2,5-Bis((tert-butoxycarbonyl)amino)pentanoic acid;N2,N5-Di-Boc-L-ornithine;(2S)-2,5-bis[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;L-Ornithine, N2,N5-bis[(1,1-dimethylethoxy)carbonyl]-;Boc-L-Orn(Boc)-OH;MFCD00151882;Nalpha,delta-Bis-Boc-L-ornithine;Boc-Orn(Boc);(2S)-2,5-Bis({[(Tert-Butoxy)Carbonyl]Amino})Pentanoic Acid;N,N'-bis-BOC-ornithine;N,N'-Di(Boc)-L-ornithine;boc-orn(boc)-oh, AldrichCPR;SCHEMBL903957;Nalpha,Ndelta-bis-Boc-ornithine;DTXSID60426767;Nalpha,Ndelta-di-Boc-L-ornithine;RJOJSMIZZYHNQG-JTQLQIEISA-N;AKOS015841466;Di-N-(tert-butoxycarbonyl)-L-ornithine;N,N'-Di-tert-butoxycarbonyl-L-ornithine;BP-10789;DS-14736;N,N'-Di-(t-butyloxycarbonyl)-L-ornithine;N2,N5-bis(tert-butoxycarbonyl)-L-ornithine;CS-0154371;O11703;N-alpha-N'-Di-(t-butyloxycarbonyl)-L-ornithine;A831323;(S)-2,5-bis(tert-butoxycarbonylamino)pentanoic acid

Chemical Property of Boc-orn(boc)-OH

Chemical Property:

• Vapor Pressure: 1.58E-11mmHg at 25°C
• Boiling Point: 504.1 °C at 760 mmHg
• PKA: 3.96±0.21(Predicted)
• Flash Point: 258.7 °C
• PSA: 113.96000
• Density: 1.123 g/cm³
• LogP: 3.05100
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 332.19473662
• Heavy Atom Count: 23
• Complexity: 423

Purity/Quality:

98%min ^*data from raw suppliers

boc-orn(boc)-oh AldrichCPR ^*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)OC(C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)NCCC[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• Uses: Boc-Orn(Boc)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Technology Process of Boc-orn(boc)-OH

There total 3 articles about Boc-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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-α-ornithine hydrochloride (36630-89-4) → (S)-2,5-bis((tert-butoxycarbonyl)amino)pentanoic acid (57133-29-6)

Guidance literature:

(S)-α-ornithine hydrochloride; With sodium hydroxide; In water; at 0 ℃; for 0.25h;

di-tert-butyl dicarbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2014.05.087

Reference yield: 98.0%

L-ornithine (70-26-8,25104-12-5,410523-47-6) + di-tert-butyl dicarbonate (24424-99-5) → (S)-2,5-bis((tert-butoxycarbonyl)amino)pentanoic acid (57133-29-6)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 50 ℃; for 3h;

DOI:10.1039/c3ob40162f

Reference yield: 96.0%

di-tert-butyl dicarbonate (24424-99-5) + L-ornithine hydrochloride (3184-13-2,36630-89-4) → (S)-2,5-bis((tert-butoxycarbonyl)amino)pentanoic acid (57133-29-6)

Guidance literature:

With triethylamine; In water; acetone; at 20 ℃; for 12h;

DOI:10.1016/j.cclet.2017.10.015

upstream raw materials:

L-ornithine

di-tert-butyl dicarbonate

L-ornithine hydrochloride

(S)-α-ornithine hydrochloride

Downstream raw materials:

Boc-Orn(Boc)-β-Ala-OBzl

[4-tert-butoxycarbonylamino-4-(4-sulfamoyl-benzylcarbamoyl)-butyl]-carbamic acid tert-butyl ester

Boc-Orn(Boc)-amN

(2R)-3-{4-[2-amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulphanyl)-3,5-dicyanopyridin-4-yl]phenoxy}propane-1,2-diyl(2S,2'S)-bis{2,5-bis[(tert-butoxycarbonyl)amino]pentanoate}

Refernces

• 1、 Sun, Haiyang,Li, Hui,Wang, Jiayi,Song, Gonghua. "Synthesis and nematicidal activity of piperazinedione derivatives based on the natural product Barettin". . p. 977 - 980. Retrieved 2017/11/16.
• 2、 ?ula, Ale?,Kikelj, Danijel,Ila?, Janez. "A convenient strategy for synthesizing the Agelas alkaloids clathrodin, oroidin, and hymenidin and their (un)saturated linker analogs". supporting information. p. 3999 - 4001. Retrieved 2014/07/08.