Z-Glu-phe-OH

Base Information

• Chemical Name: Z-Glu-phe-OH
• CAS No.: 987-84-8
• Molecular Formula: C22H24 N2 O7
• Molecular Weight: 428.442
• European Community (EC) Number: 213-581-2
• Nikkaji Number: J298.587J
• Mol file: 987-84-8.mol

Synonyms:Z-GLU-PHE-OH;987-84-8;(4S)-5-[[(1S)-1-carboxy-2-phenylethyl]amino]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid;SCHEMBL1426719;MFCD00037262;Carbobenzoxy-L-glu tamyl-L-phenylalanin;s12378;BS-42462;CS-0363198;NS00042556;L-Phenylalanine,N-[(phenylmethoxy)carbonyl]-L-a-glutamyl-;(S)-4-(benzyloxycarbonylamino)-5-((S)-1-carboxy-2-phenylethylamino)-5-oxopentanoic acid;(S)-4-(((benzyloxy)carbonyl)amino)-5-(((S)-1-carboxy-2-phenylethyl)amino)-5-oxopentanoic acid

Chemical Property of Z-Glu-phe-OH

Chemical Property:

• Vapor Pressure: 2.62E-24mmHg at 25°C
• Boiling Point: 760.4 °C at 760 mmHg
• Flash Point: 413.7 °C
• PSA: 142.03000
• Density: 1.325 g/cm³
• LogP: 2.74010
• Storage Temp.: -15°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 428.15835111
• Heavy Atom Count: 31
• Complexity: 613

Purity/Quality:

99% ^*data from raw suppliers

Z-Glu-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)O)NC(=O)C(CCC(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)OCC2=CC=CC=C2

Technology Process of Z-Glu-phe-OH

There total 14 articles about Z-Glu-phe-OH 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: 88.0%

benzyl N-[(1S)-1-acetyl-4-(1H-1,2,3-benzotriazol-1-yl)-4-oxobutyl]carbamate (886981-21-1) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (4S)-4-{[(benzyloxy)carbonyl]amino}-5-{[(1S)-1-carboxy-2-phenylethyl]amino}-5-oxopentanoic acid (987-84-8)

Guidance literature:

With triethylamine; In water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1055/s-2006-926287

Reference yield: 49.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + Z-L-GluOMe (5672-83-3) → (4S)-4-{[(benzyloxy)carbonyl]amino}-5-{[(1S)-1-carboxy-2-phenylethyl]amino}-5-oxopentanoic acid (987-84-8)

Guidance literature:

With Staphylococcus aureus V₈ proteinase; triethylamine; In water; acetonitrile; at 30 ℃; for 4h;

DOI:10.1016/S0040-4039(00)92725-4

Reference yield:

N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) → (4S)-4-{[(benzyloxy)carbonyl]amino}-5-{[(1S)-1-carboxy-2-phenylethyl]amino}-5-oxopentanoic acid (987-84-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: SOCl₂ / tetrahydrofuran / 0.33 h / 40 - 50 °C

1.2: 92 percent / tetrahydrofuran / 2 h / 20 °C

2.1: 88 percent / Et₃N / acetonitrile; H₂O / 1 h / 20 °C

With thionyl chloride; triethylamine; In tetrahydrofuran; water; acetonitrile;

DOI:10.1055/s-2006-926287

upstream raw materials:

N-(N-benzyloxycarbonyl-α-L-glutamyl)-L-phenylalanine ethyl ester

Z-α-Glu-Phe-O-t-Bu

L-phenylalanine

Z-L-GluOMe

Downstream raw materials:

N-benzyloxycarbonyl-L-isoglutamine

N-γ-L-glutamyl-L-phenylalanine