Z-Phe-ONp

Base Information

• Chemical Name: Z-Phe-ONp
• CAS No.: 2578-84-9
• Molecular Formula: C23H20 N2 O6
• Molecular Weight: 420.422
• European Community (EC) Number: 219-938-9
• DSSTox Substance ID: DTXSID70948647
• Nikkaji Number: J80.521A
• Wikidata: Q82926464
• ChEMBL ID: CHEMBL3278846
• Mol file: 2578-84-9.mol

Synonyms:benzyloxycarbonylphenylalanine 4-nitrophenyl ester;benzyloxycarbonylphenylalanine 4-nitrophenyl ester, (D)-isomer;benzyloxycarbonylphenylalanine 4-nitrophenyl ester, (L)-isomer;Z-Phe-4-NPE

Chemical Property of Z-Phe-ONp

Chemical Property:

• Vapor Pressure: 1.35E-15mmHg at 25°C
• Melting Point: 126-127oC
• Boiling Point: 626.2°Cat760mmHg
• PKA: 10.62±0.46(Predicted)
• Flash Point: 332.5°C
• PSA: 110.45000
• Density: 1.303g/cm³
• LogP: 4.95200
• Storage Temp.: -15°C
• Solubility.: Dichloromethane; Methanol
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 420.13213636
• Heavy Atom Count: 31
• Complexity: 587

Purity/Quality:

98%min ^*data from raw suppliers

Z-L-phenylalanine 4-nitrophenyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)OC2=CC=C(C=C2)[N+](=O)[O-])NC(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)OC2=CC=C(C=C2)[N+](=O)[O-])NC(=O)OCC3=CC=CC=C3

Technology Process of Z-Phe-ONp

There total 15 articles about Z-Phe-ONp 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%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N-Cbz-L-Phe (1161-13-3) → N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester (2578-84-9)

Guidance literature:

With N,N'-Bis(2-oxo-3-oxazolidinyl)phosphorodiamidic azide; triethylamine; In dichloromethane;

Reference yield: 68.0%

N-Cbz-L-Phe (1161-13-3) + 4-Nitrophenyl chloroformate (7693-46-1) → N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester (2578-84-9)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 4 ℃; for 0.833333h;

DOI:10.1016/j.bmc.2006.09.011

Reference yield: 53.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + i-propyl isocyanide (598-45-8) + N-Cbz-L-Phe (1161-13-3) → N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester (2578-84-9)

Guidance literature:

In ethanol; ethyl acetate;

upstream raw materials:

tris(p-nitrophenyl)-phosphite

N-Cbz-L-Phe

4-nitro-phenol

dicyclohexyl-carbodiimide

Downstream raw materials:

phenylalanine-(4-nitro-phenyl ester); hydrobromide

(S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-methylbutanoate

Z-Phe-Glu(OCMe₃)-OCH₃

N-Z-L-phenylalanyl-L-valine methylester

Refernces

• 1、 Kokkala, Paraskevi,Mpakali, Anastasia,Mauvais, Francois-Xavier,Papakyriakou, Athanasios,Daskalaki, Ira,Petropoulou, Ioanna,Kavvalou, Sofia,Papathanasopoulou, Mirto,Agrotis, Stefanos,Fonsou, Theodora-Markisia,Van Endert, Peter,Stratikos, Efstratios,Georgiadis, Dimitris. "Optimization and Structure-Activity Relationships of Phosphinic Pseudotripeptide Inhibitors of Aminopeptidases That Generate Antigenic Peptides". supporting information. p. 9107 - 9123. Retrieved 2016/10/22.
• 2、 -. "NOVEL ARYLAMIDINE DERIVATIVE OR SALT THEREOF". Page 116-117. . Retrieved 2010/02/09.