Z-Phe-osu

Base Information

• Chemical Name: Z-Phe-osu
• CAS No.: 3397-32-8
• Molecular Formula: C21H20N2O6
• Molecular Weight: 396.4
• European Community (EC) Number: 222-254-3
• Nikkaji Number: J80.715J
• Mol file: 3397-32-8.mol

Synonyms:Z-PHE-OSU;3397-32-8;MFCD00053549;2,5-dioxopyrrolidin-1-yl ((benzyloxy)carbonyl)-L-phenylalaninate;(S)-2,5-Dioxopyrrolidin-1-yl 2-(((benzyloxy)carbonyl)amino)-3-phenylpropanoate;ZPheOSu;SCHEMBL5689118;MOJNKVWQJKPXCT-KRWDZBQOSA-N;AKOS016369135;AS-46896;CS-0451371;NS00049324;F10850;n-benzyloxycarbonylphenylalanine n-hydroxysuccinimide ester;2,5-DIOXOPYRROLIDIN-1-YL (2S)-2-{[(BENZYLOXY)CARBONYL]AMINO}-3-PHENYLPROPANOATE;N-alpha-BenZyloxycarbonyl-L-phenylalanine succinimidyl ester (CbZ-L-Phe-OSu)

Chemical Property of Z-Phe-osu

Chemical Property:

• Melting Point: 140-140.5 °C
• Refractive Index: 1.617
• PKA: 10.56±0.46(Predicted)
• PSA: 102.01000
• Density: 1.35 g/cm³
• LogP: 2.46010
• Storage Temp.: -15°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 396.13213636
• Heavy Atom Count: 29
• Complexity: 594

Purity/Quality:

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

Z-L-phenylalanine N-hydroxysuccinimide ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)C(CC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1CC(=O)N(C1=O)OC(=O)[C@H](CC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3

Technology Process of Z-Phe-osu

There total 8 articles about Z-Phe-osu 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: 96.0%

N-Cbz-L-Phe (1161-13-3) + 1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate (107960-02-1) → N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester (3397-32-8)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; acetonitrile; Ambient temperature;

DOI:10.1021/jo00388a005

Reference yield: 95.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-Cbz-L-Phe (1161-13-3) → N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester (3397-32-8)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃; for 18h;

DOI:10.1016/j.bmc.2010.07.041

Reference yield: 69.0%

di(succinimido) carbonate (74124-79-1) + N-Cbz-L-Phe (1161-13-3) → N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester (3397-32-8)

Guidance literature:

With dmap; In neat (no solvent); for 1h; Milling;

DOI:10.1021/jo500463y

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

N-Cbz-L-Phe

N,N’-disuccinimidyl oxalate

Isopropenyl Succinimido Carbonate

Downstream raw materials:

N-Benzyloxycarbonyl-Phe-Val-tert.-butyloxycarbonyl-hydrazid

[(N-benzyloxycarbonyl-L-phenylalanyl-L-phenylalanyl)amino]-methylphosphonic acid

(S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-(4-hydroxyphenyl)propanoate

(1R)-1-[(N-benzyloxycarbonyl-L-phenylalanyl)amino]-ethylphosphonic acid

Refernces

• 1、 Wadhavane, Prashant D.,Izquierdo, M. Angeles,Lutters, Dennis,Burguete, M. Isabel,Marin, Maria J.,Russell, David A.,Galindo, Francisco,Luis, Santiago V.. "Fluorescent macrocyclic probes with pendant functional groups as markers of acidic organelles within live cells". . p. 823 - 831. Retrieved 2014.
• 2、 -. "2-methoxy estradiol analogs and method for preparation thereof and use". Paragraph 0045; 0051; 0058. . Retrieved 2016/11/09.
• 3、 Berdugo, Cristina,Escuder, Beatriu,Miravet, Juan F.. "Structural insight into the aggregation of l-prolyl dipeptides and its effect on organocatalytic performance". supporting information. p. 592 - 600. Retrieved 2015/02/18.