2-(phenylmethoxycarbonylamino)-5-[phenylmethoxycarbonyl-(N'-phenylmethoxycarbonylcarbamimidoyl)amino]pentanoic acid

Base Information

• Chemical Name: 2-(phenylmethoxycarbonylamino)-5-[phenylmethoxycarbonyl-(N'-phenylmethoxycarbonylcarbamimidoyl)amino]pentanoic acid
• CAS No.: 14611-34-8
• Molecular Formula: C30H32 N4 O8
• Molecular Weight: 576.606
• Mol file: 14611-34-8.mol

Synonyms:(2S)-2-(phenylmethoxycarbonylamino)-5-[phenylmethoxycarbonyl-[(e)-n'-phenylmethoxycarbonylcarbamimidoyl]amino]pentanoic acid;2-(phenylmethoxycarbonylamino)-5-[phenylmethoxycarbonyl-(N'-phenylmethoxycarbonylcarbamimidoyl)amino]pentanoic acid;C30H32N4O8;Tri-Cbz-L-arginine;C30-H32-N4-O8;NSC 120011;tris-(Carbobenzoxy)-L-arginine;CS-W008487;HY-W008487;(S)-2-(((Benzyloxy)carbonyl)amino)-5-(1,3-bis((benzyloxy)carbonyl)guanidino)pentanoic acid;Nalpha,Nomega,Nomega'-Tris-Z-L-arginine;T0755;M03029;W-108129

Chemical Property of 2-(phenylmethoxycarbonylamino)-5-[phenylmethoxycarbonyl-(N'-phenylmethoxycarbonylcarbamimidoyl)amino]pentanoic acid

Chemical Property:

• Melting Point: 137-140°C
• Refractive Index: 1.595
• Boiling Point: °Cat760mmHg
• PKA: 3.94±0.21(Predicted)
• Flash Point: °C
• PSA: 167.35000
• Density: 1.27 g/cm3
• LogP: 5.52770
• Storage Temp.: -15°C
• Solubility.: almost transparency in hot Methanol
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 16
• Exact Mass: 576.22201399
• Heavy Atom Count: 42
• Complexity: 896

Purity/Quality:

99% ^*data from raw suppliers

Tris(carbobenzoxy)-L-arginine >98.0%(HPLC) ^*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)NC(CCCN(C(=NC(=O)OCC2=CC=CC=C2)N)C(=O)OCC3=CC=CC=C3)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CCCN(/C(=N/C(=O)OCC2=CC=CC=C2)/N)C(=O)OCC3=CC=CC=C3)C(=O)O
• Uses: Tris(carbobenzoxy)-L-arginine is a protected L-argenine derivative used in the preparation of synthetic peptides and amides, such as argiopine.

Technology Process of 2-(phenylmethoxycarbonylamino)-5-[phenylmethoxycarbonyl-(N'-phenylmethoxycarbonylcarbamimidoyl)amino]pentanoic acid

There total 8 articles about 2-(phenylmethoxycarbonylamino)-5-[phenylmethoxycarbonyl-(N'-phenylmethoxycarbonylcarbamimidoyl)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: 64.0%

Z-Arg-OH (1234-35-1) + benzyl chloroformate (501-53-1,94274-21-2) → Nα,Nδ,Nω-tris(benzyloxycarbonyl)-L-arginine (14611-34-8)

Guidance literature:

Z-Arg-OH; With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine;

benzyl chloroformate;

DOI:10.1134/S1068162009060120

Reference yield: 58.0%

L-arginine (74-79-3,25212-18-4) + benzylpentachlorophenyl carbonate (13795-28-3) → Nα,Nδ,Nω-tris(benzyloxycarbonyl)-L-arginine (14611-34-8)

Guidance literature:

With bis-(trimethylsilyl)acetamide;

Reference yield: 49.0%

L-arginine (74-79-3,25212-18-4) + benzyl chloroformate (501-53-1,94274-21-2) → Nα,Nδ,Nω-tris(benzyloxycarbonyl)-L-arginine (14611-34-8)

Guidance literature:

With sodium hydroxide; at -10 ℃;

upstream raw materials:

L-arginine

Z-Arg-OH

benzyl chloroformate

benzylpentachlorophenyl carbonate

Downstream raw materials:

N-(N^α,N^δ,N^ω-tris-benzyloxycarbonyl-L-arginyl)-L-glutamic acid dibenzyl ester

N^ω-benzyloxycarbonyl-N^α-(N^α,N^δ,N^ω-tris-benzyloxycarbonyl-L-arginyl)-L-arginine benzyl ester

H-Arg(Z)2-OH

N^α,N^δ,N^ω-tris-benzyloxycarbonyl-L-arginine amide

Refernces

• 1、 Moynihan, Humphrey A.,Yu, Weiping. "Alkoxycarbonylation and selective deprotection of N-silyl derivatives of L-arginine". . p. 3349 - 3352. Retrieved 2007/10/03.
• 2、 Orlowska, Alicja,Drabarek, Stefania. "INVESTIGATION ON PEPTIDE SYNTHESIS BY FRAGMENT CONDENSATION. PART I. SYNTHESIS OF C1 - C4 FRAGMENT OF SUBSTANCE P IN SOLUTION AND BY THE SOLID PHASE METHOD". . p. 1893 - 1899. Retrieved 2007/10/02.