Boc-Orn-OH

Base Information

• Chemical Name: Boc-Orn-OH
• CAS No.: 21887-64-9
• Molecular Formula: C10H20N2O4
• Molecular Weight: 232.28
• Hs Code.: 29224999
• European Community (EC) Number: 663-892-6
• DSSTox Substance ID: DTXSID50427026
• Nikkaji Number: J775.777H
• Wikidata: Q72450212
• Mol file: 21887-64-9.mol

Synonyms:Boc-Orn-OH;21887-64-9;Boc-L-ornithine;(2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic Acid;L-5-AMINO-2-N-BOC-AMINO-PENTANOIC ACID;L-Ornithine, N2-[(1,1-dimethylethoxy)carbonyl]-;(S)-5-Amino-2-tert-butoxycarbonylamino-pentanoic acid;(S)-5-amino-2-((tert-butoxycarbonyl)amino)pentanoic acid;(S)-5-amino-2-(tert-butoxycarbonylamino)pentanoic acid;(2S)-5-azaniumyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate;MFCD00076970;N-Boc-L-ornithine;Boc-Orn--OH;Nalpha -BOC-L-ornithine;SCHEMBL1487792;DTXSID50427026;AMPVNPYPOOQUJF-ZETCQYMHSA-N;Boc-Orn-OH, >=98% (TLC);Nalpha-tert-Butyloxycarbonyl-ornitine;N2-(tert-Butoxycarbonyl)-L-ornithine;AKOS005259526;AKOS015909364;AM82606;CS-W012935;AS-18960;EN300-268561;M03343;L-5-Amino-2-tert-butoxycarbonylamino-pentanoic acid;5-amino-2-(tert-butoxycarbonyl)pentanoic acid;(2S)-5-amino-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid

Chemical Property of Boc-Orn-OH

Chemical Property:

• Vapor Pressure: 1.77E-07mmHg at 25°C
• Melting Point: 207-208℃
• Refractive Index: 1.486
• Boiling Point: 398.9 °C at 760 mmHg
• PKA: 3.85±0.21(Predicted)
• Flash Point: 195.1 °C
• PSA: 101.65000
• Density: 1.135 g/cm³
• LogP: 1.79440
• Storage Temp.: Store at RT.
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 232.14230712
• Heavy Atom Count: 16
• Complexity: 248

Purity/Quality:

99% ^*data from raw suppliers

BOC-ORN-OH 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37-60-37-24

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCCN)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCCN)C(=O)O
• Uses: Nα-Boc-L-Ornithine, is a boc-protected analogue of L-Orthinine (O695550), a non essential amino acid and intermediate in arginine biosynthesis. It can be used in the enzymatic preparation of N-BOC-5-hydroxy-L-proline, and N-Cbz-5-hydroxy-L-proline, which are alternative key intermediates for the synthesis of Saxagliptin (S143500), used for the treatment of type II diabetes mellitus.

Technology Process of Boc-Orn-OH

There total 19 articles about Boc-Orn-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: 100.0%

Boc-Orn(Z)-OH (2480-93-5) → N2-(tert-butoxycarbonyl)-L-ornithine (21887-64-9)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; In methanol; water; under 1810.02 - 2585.7 Torr;

DOI:10.1021/jm960572n

Reference yield: 98.0%

Nα-tert-butoxycarbonyl ε-benzoyl-L-ornithine → N2-(tert-butoxycarbonyl)-L-ornithine (21887-64-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 22h;

Reference yield: 96.0%

L-ornithine (70-26-8,25104-12-5,410523-47-6) + di-tert-butyl dicarbonate (24424-99-5) → N2-(tert-butoxycarbonyl)-L-ornithine (21887-64-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 12h;

DOI:10.1039/d1ob00798j

upstream raw materials:

Boc-Orn(Cbz)-OH

Boc-Orn(Z)-OH

L-ornithine hydrochloride

tert-butyl 1H-benzo[d][1,2,3]triazole-1-carboxylate

Downstream raw materials:

N(α)-tert.-Butyloxycarbonyl-N(δ)-((R)-6-methyloctanoyl)-L-ornithin-p-nitrophenylester

N^α-Boc-N^δ-((cyanimino)phenoxymethyl)-L-ornithine

tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate

(2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoic acid

Refernces

• 1、 Hazra, Bibhas,Prasad, Mahesh,Roy, Rajat,Tarafdar, Pradip K.. "The microenvironment and pKaperturbation of aminoacyl-tRNA guided the selection of cationic amino acids". supporting information. p. 8049 - 8056. Retrieved 2021/10/04.
• 2、 Cramer, Jonathan,Klebe, Gerhard. "An Allyl Protection and Improved Purification Strategy Enables the Synthesis of Functionalized Phosphonamidate Peptides". supporting information. p. 1857 - 1866. Retrieved 2017/04/06.