Benzyl N-[(benzyloxy)carbonyl]glycylphenylalaninate

Base Information

• Chemical Name: Benzyl N-[(benzyloxy)carbonyl]glycylphenylalaninate
• CAS No.: 24117-97-3
• Molecular Formula: C26H26 N2 O5
• Molecular Weight: 446.503
• NSC Number: 169139
• DSSTox Substance ID: DTXSID80305106
• Mol file: 24117-97-3.mol

Synonyms:24117-97-3;NSC169139;Benzyl N-[(benzyloxy)carbonyl]glycylphenylalaninate;DTXSID80305106;AKOS024432481;NSC-169139;benzyl (2S)-2-[({[(benzyloxy)carbonyl]amino}acetyl)amino]-3-phenylpropanoate

Chemical Property of Benzyl N-[(benzyloxy)carbonyl]glycylphenylalaninate

Chemical Property:

• Vapor Pressure: 6.68E-18mmHg at 25°C
• Boiling Point: 671.7°C at 760 mmHg
• Flash Point: 360°C
• Density: 1.224g/cm³
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 446.18417193
• Heavy Atom Count: 33
• Complexity: 608

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)OCC2=CC=CC=C2)NC(=O)CNC(=O)OCC3=CC=CC=C3

Technology Process of Benzyl N-[(benzyloxy)carbonyl]glycylphenylalaninate

There total 9 articles about Benzyl N-[(benzyloxy)carbonyl]glycylphenylalaninate 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%

L-phenylalanine benzyl ester p-toluene-sulfonic acid salt (1738-78-9) + N-(Benzyloxycarbonyl)glycine (1138-80-3) → Z-Gly-L-Phe-OBzl (24117-97-3) + 2-(2-tert-butoxycarbonylamino-acetylamino)-3-phenyl-propionic acid benzyl ester (5519-03-9)

Guidance literature:

With potassium hydroxide; bis(o-nitrophenyl)phenylphosphonate; 4 A molecular sieve; trithylamine; tetrabutylammomium bromide; other acids; multistep reaction;

DOI:10.1246/cl.1981.285

Reference yield: 83.0%

Z-Gly-(L)-Phe (1170-76-9) → Z-Gly-L-Phe-OBzl (24117-97-3)

Guidance literature:

With potassium carbonate; In dichloromethane; for 8h; Ambient temperature;

DOI:10.1246/bcsj.69.1099

Reference yield:

L-Phenylalanine benzyl ester (962-39-0) + Benzyloxycarbonylamino-acetic acid 6-nitro-benzotriazol-1-yl ester → Z-Gly-L-Phe-OBzl (24117-97-3)

Guidance literature:

With triethylamine; In acetonitrile; for 1h; Yield given; Ambient temperature;

DOI:10.1055/s-1983-30215

upstream raw materials:

N-(benzyloxycarbonyl)glycyl chloride

ethynyl methyl ether

L-Phenylalanine benzyl ester

N-(Benzyloxycarbonyl)glycine

Downstream raw materials:

Gly-Phe-OH

N-glycyl-L-phenylalanine benzyl ester; hydrobromide

N-benzyloxycarbonyl-glycyl=>glycyl=>phenylalanine benzyl ester; N-benzyloxycarbonyl-glycyl=>glycyl=>L-phenylalanine benzyl ester

ethyl N-benzyloxycarbonylglycyl-L-phenylalanylglycinate

Refernces

• 1、 Furukawa, M.,Hokama, N.,Okawara, T.. "1-(2-Nitrobenzenesulfonyloxy)-6-nitrobenzotriazole: A New Reagent for Coupling in Peptide Synthesis". . p. 42 - 44. Retrieved 2007/10/02.