3-Phenyl-N-(3-phenyl-N-((phenylmethoxy)carbonyl)-L-alanyl)-L-alanine

Base Information

• Chemical Name: 3-Phenyl-N-(3-phenyl-N-((phenylmethoxy)carbonyl)-L-alanyl)-L-alanine
• CAS No.: 13122-91-3
• Molecular Formula: C26H26 N2 O5
• Molecular Weight: 446.503
• European Community (EC) Number: 236-051-2
• UNII: Q3HUG35MZD
• DSSTox Substance ID: DTXSID10156961
• Nikkaji Number: J208.280B
• Wikidata: Q83025085
• Pharos Ligand ID: 7QZ2ZUX6FK81
• ChEMBL ID: CHEMBL36801
• Mol file: 13122-91-3.mol

Synonyms:13122-91-3;Z-Phe-Phe-OH;N-Carbobenzoxy-L-phenylalanyl-L-phenylalanine;3-Phenyl-N-(3-phenyl-N-((phenylmethoxy)carbonyl)-L-alanyl)-L-alanine;(2S)-3-phenyl-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoic acid;Q3HUG35MZD;CHEMBL36801;EINECS 236-051-2;(S)-2-((S)-2-(((Benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-phenylpropanoic acid;((Benzyloxy)carbonyl)-L-phenylalanyl-L-phenylalanine;3-phenyl-N-[3-phenyl-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-alanine;C26-H26-N2-O5;Z-Phe-Phe-H;UNII-Q3HUG35MZD;MLS001243463;SCHEMBL7319412;DTXSID10156961;HMS2211G08;L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-L-phenylalanyl-;N-(Benzyloxycarbonyl)-Phe-Phe-OH;BDBM50284780;MFCD00191139;N-Cbz-L-phenylalanyl-L-phenylalanine;NCGC00247399-01;AS-70984;SMR000841578;CS-0321047;T70203;A888559;N-benzyloxycarbonyl-L-phenylalanyl-L-phenyl-alanine;N-(benzyloxycarbonyl)-l-phenylala-nyl-l-phenylalanine;L-Phenylalanine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-;N-(2-([(Benzyloxy)carbonyl]amino)-3-phenylpropanoyl)phenylalanine #;(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanamido]-3-phenylpropanoic acid;(S)-2-((S)-2-(benzyloxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoic acid

Chemical Property of 3-Phenyl-N-(3-phenyl-N-((phenylmethoxy)carbonyl)-L-alanyl)-L-alanine

Chemical Property:

• Vapor Pressure: 2.21E-22mmHg at 25°C
• Melting Point: 159 °C
• Refractive Index: -10 ° (C=1, MeOH)
• Boiling Point: 730.2°Cat760mmHg
• PKA: 3.53±0.10(Predicted)
• Flash Point: 395.4°C
• PSA: 104.73000
• Density: 1.253g/cm³
• LogP: 4.11800
• Storage Temp.: -15°C
• Solubility.: almost transparency in Methanol
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 446.18417193
• Heavy Atom Count: 33
• Complexity: 622

Purity/Quality:

98%,99%, ^*data from raw suppliers

Z-Phe-Phe-OH ^*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)NC(CC2=CC=CC=C2)C(=O)O)NC(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O)NC(=O)OCC3=CC=CC=C3
• Uses: Substrate for cathepsin A.

Technology Process of 3-Phenyl-N-(3-phenyl-N-((phenylmethoxy)carbonyl)-L-alanyl)-L-alanine

There total 33 articles about 3-Phenyl-N-(3-phenyl-N-((phenylmethoxy)carbonyl)-L-alanyl)-L-alanine 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: 98.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + (S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate (769922-77-2) → N-benzyloxycarbonyl-L-phenylalanyl-L-phenylalanine (13122-91-3)

Guidance literature:

With triethylamine; In water; acetonitrile; at 20 ℃;

DOI:10.1055/s-2004-831255

Reference yield: 94.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + (S)-benzyloxycarbonylphenylalanine pentafluorophenyl ester (17543-49-6) → N-benzyloxycarbonyl-L-phenylalanyl-L-phenylalanine (13122-91-3)

Guidance literature:

With calcium(II) nitrate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield: 80.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + N-Cbz-L-Phe (1161-13-3) → N-benzyloxycarbonyl-L-phenylalanyl-L-phenylalanine (13122-91-3)

Guidance literature:

N-Cbz-L-Phe; With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at 0 ℃; for 0.5h; Green chemistry;

L-phenylalanine; With water; In tetrahydrofuran; at 0 ℃; for 0.5h; Green chemistry;

DOI:10.1016/j.tetasy.2016.11.009

upstream raw materials:

Z-Phe-Phe-OEt(Br)

N-(benzyloxycarbonyl)-L-phenylalanyl-L-phenylalanine methyl ester

Boc-Phe-Phe-OPet

Phe-Phe

Downstream raw materials:

Boc-Phe-Phe-OPet

1-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-cyclopentanecarboxylic acid ethyl ester

Z-Phe-Phe-Ser(OBzl)(OMe)

(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester

Refernces

• 1、 Zhao, De-Yin,Zhang, Ming-Xia,Dong, Xiao-Wu,Hu, Yong-Zhou,Dai, Xiao-Yan,Wei, Xiaoyi,Hider, Robert C.,Zhang, Jin-Chao,Zhou, Tao. "Design and synthesis of novel hydroxypyridinone derivatives as potential tyrosinase inhibitors". . p. 3103 - 3108. Retrieved 2016.
• 2、 Matsumoto, Takuya,Sasamoto, Koki,Hirano, Ryo,Oisaki, Kounosuke,Kanai, Motomu. "A catalytic one-step synthesis of peptide thioacids: the synthesis of leuprorelin via iterative peptide-fragment coupling reactions". supporting information. p. 12222 - 12225. Retrieved 2018/12/01.
• 3、 Mukherjee, Jyoti Prasad,Sil, Suman,Pahari, Amit K.,Chattopadhyay, Shital K.. "A Modular Synthesis of Some Biologically Relevant Cyclic Peptides through Late-Stage Functionalization". . p. 1181 - 1190. Retrieved 2016/05/11.