(R)-2-Amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid

Base Information

• Chemical Name: (R)-2-Amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid
• CAS No.: 16937-91-0
• Molecular Formula: C13H18N2O4
• Molecular Weight: 266.297
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID30428495
• Nikkaji Number: J307.688A
• Mol file: 16937-91-0.mol

Synonyms:16937-91-0;H-D-ORN(Z)-OH;(R)-2-Amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid;Ndelta-Z-D-ornithine;(2R)-2-amino-5-(phenylmethoxycarbonylamino)pentanoic acid;N-Delta-Cbz-D-ornithine;D-Ornithine, N5-[(phenylmethoxy)carbonyl]-;N~5~-[(Benzyloxy)carbonyl]-D-ornithine;MFCD00063115;SCHEMBL2677967;DTXSID30428495;VULSXQYFUHKBAN-LLVKDONJSA-N;AKOS015889954;CS-W022744;Ndelta -(benzyloxycarbonyl)-D-ornithine;DS-16372;(R)-N5 -(phenylmethoxycarbonyl)-ornithine;EN300-6759661;A882098;J-010532;(R)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid;(2R)-2-AMINO-5-{[(BENZYLOXY)CARBONYL]AMINO}PENTANOIC ACID

Chemical Property of (R)-2-Amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid

Chemical Property:

• Boiling Point: 489.4 °C at 760 mmHg
• Flash Point: 249.8 °C
• PSA: 101.65000
• Density: 1.234 g/cm³
• LogP: 2.19610
• Storage Temp.: Store at RT.
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 266.12665706
• Heavy Atom Count: 19
• Complexity: 290

Purity/Quality:

98.5% ^*data from raw suppliers

H-D-Orn(Z)-OH 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NCCCC(C(=O)O)N
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)NCCC[C@H](C(=O)O)N

Technology Process of (R)-2-Amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid

There total 6 articles about (R)-2-Amino-5-(((benzyloxy)carbonyl)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: 95.0%

(R)-Nδ-benzyloxycarbonyl-Nα-(tert-butoxycarbonyl)-ornithine (2480-93-5,16937-92-1) → Nε-(benzyloxycarbonyl)ornithine (16937-91-0,118578-06-6)

Guidance literature:

With phosphoric acid; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jo061377b

Reference yield: 88.0%

For-D-Orn(Z)-OH (70671-55-5) → Nε-(benzyloxycarbonyl)ornithine (16937-91-0,118578-06-6)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 50 ℃; for 9h;

DOI:10.1246/bcsj.61.575

Reference yield: 83.0%

D-ornithine hydrochloride (16682-12-5,36630-89-4) + benzyl chloroformate (501-53-1,94274-21-2) → Nε-(benzyloxycarbonyl)ornithine (16937-91-0,118578-06-6)

Guidance literature:

D-ornithine hydrochloride; benzyl chloroformate; With copper(ll) sulfate pentahydrate; potassium carbonate; sodium hydroxide; In toluene; at 20 ℃; Cooling with ice;

With titriplex III; In water; at 100 ℃; for 1h;

DOI:10.1021/jm801018u

upstream raw materials:

For-D-Orn(Z)-OH

(R)-Nδ-benzyloxycarbonyl-Nα-(tert-butoxycarbonyl)-ornithine

For-DL-Orn(Z)-OH

D-ornithine hydrochloride

Downstream raw materials:

N-acetylornithine

(R)-Nδ-benzyloxycarbonyl-Nα-(tert-butoxycarbonyl)-ornithine

L-β-benzyloxypropionyl-carbobenzoxyrnithine

N^α-p-toluenesulfonyl-N^δ-(benzyloxycarbonyl)-D-ornithine

Refernces

• 1、 Keller, Max,Pop, Nathalie,Hutzler, Christoph,Beck-Sickinger, Annette G.,Bernhardt, Günther,Buschauer, Armin. "Guanidine-acylguanidine bioisosteric approach in the design of radioligands: Synthesis of a tritium-labeled NG-propionylargininamide ([3H]-UR-MK114) as a highly potent and selective neuropeptide Y Y1 receptor antagonist". supporting information; experimental part. p. 8168 - 8172. Retrieved 2009/12/07.
• 2、 Kang, Shinwon,Minematsu, Yoshihiro,Shimohigashi, Yasuyuki,Waki, Michinori,Izumiya, Nobuo. "Different Acyl Specificity between Mold and Kidney Acylases: Correlation of Hydrolytic Rate to Molecular Size and Electronegative Property of Acyl Group in Acyl-L-phenylalanine Hydrolysis". . p. 575 - 576. Retrieved 2007/10/02.