Cbz-L-Phenylalaninal

Base Information

• Chemical Name: Cbz-L-Phenylalaninal
• CAS No.: 59830-60-3
• Molecular Formula: C17H17NO3
• Molecular Weight: 283.327
• DSSTox Substance ID: DTXSID40427338
• Nikkaji Number: J443.617B
• Wikidata: Q72440874
• ChEMBL ID: CHEMBL412423
• Mol file: 59830-60-3.mol

Synonyms:Cbz-L-Phenylalaninal;59830-60-3;(S)-Benzyl (1-oxo-3-phenylpropan-2-yl)carbamate;benzyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate;CHEMBL412423;(1-Benzyl-2-oxo-ethyl)-carbamic acid benzyl ester;(S)-(-)-2-(Benzylcarbonylamino)-3-phenylpropanal;N-Cbz-phenylalaninal;N-Cbz-L-Phenylalaninal;D0N6QM;SCHEMBL630290;DTXSID40427338;HZDPJHOWPIVWMR-INIZCTEOSA-N;n-benzyloxycarbonyl-l-phenylalaninal;BDBM50014568;MFCD00798796;AKOS005146049;AC-23793;DS-14328;N-((Benzyloxy)carbonyl)-L-phenylalaninal;PD177889;N-(((Benzyl)oxy)carbonyl)-L-phenylalaninal;CS-0062211;I11555;A869110;benzyl (S)-(1-oxo-3-phenylpropan-2-yl)carbamate;((S)-1-Benzyl-2-oxo-ethyl)-carbamic acid benzyl ester

Chemical Property of Cbz-L-Phenylalaninal

Chemical Property:

• Boiling Point: 450.4 °C at 760 mmHg
• Flash Point: 226.2 °C
• PSA: 55.40000
• Density: 1.168g/cm³
• LogP: 3.11390
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 283.12084340
• Heavy Atom Count: 21
• Complexity: 320

Purity/Quality:

99%, ^*data from raw suppliers

(S)-Benzyl(1-oxo-3-phenylpropan-2-yl)carbamate 95+% ^*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(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C=O)NC(=O)OCC2=CC=CC=C2

Technology Process of Cbz-L-Phenylalaninal

There total 50 articles about Cbz-L-Phenylalaninal 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%

[(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester (114744-85-3) → benzyl (1S)-(1-formyl-2-phenylethyl)carbamate (59830-60-3)

Guidance literature:

[(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester; With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2h;

With hydrogenchloride; water; In tetrahydrofuran;

Reference yield: 100.0%

benzyl 1-benzyl-2,2-dimethoxyethylcarbamate (59830-61-4) → N-benzyloxycarbonyl-2-amino-3-phenylpropionaldehyde (59830-60-3,63219-70-5,68474-26-0)

Guidance literature:

With formic acid; water; at 20 - 25 ℃; for 8h;

Reference yield: 99.0%

N-((benzyloxy)carbonyl)-L-phenylalaninol (6372-14-1) → benzyl (1S)-(1-formyl-2-phenylethyl)carbamate (59830-60-3)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; bisacetoxybromate(I) resin; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/adsc.200202208

upstream raw materials:

rac-N-benzyloxycarbonyl-phenylalanine ethyl ester

(2S)-2-(N-benzyloxycarbonyl)-amino-3-phenyl propanol

Z-DL-Phe-OH

Phenylalanine

Downstream raw materials:

(S)-2-((S)-2-Benzyloxycarbonylamino-1-cyano-3-phenyl-propylamino)-4-methyl-pentanoic acid methyl ester

((S)-1-Benzyl-2-hydroxy-pent-4-enyl)-carbamic acid benzyl ester

((S)-1-Benzyl-2-hydroxy-propyl)-carbamic acid benzyl ester

((S)-1-Benzyl-2-hydroxy-butyl)-carbamic acid benzyl ester

Refernces

• 1、 García-Urricelqui, Ane,de Cózar, Abel,Mielgo, Antonia,Palomo, Claudio. "Probing α-Amino Aldehydes as Weakly Acidic Pronucleophiles: Direct Access to Quaternary α-Amino Aldehydes by an Enantioselective Michael Addition Catalyzed by Br?nsted Bases". . p. 2483 - 2492. Retrieved 2020/12/25.
• 2、 Wei, Binqing,Gunzner-Toste, Janet,Yao, Hui,Wang, Tao,Wang, Jing,Xu, Zijin,Chen, Jinhua,Wai, John,Nonomiya, Jim,Tsai, Siao Ping,Chuh, Josefa,Kozak, Katherine R.,Liu, Yichin,Yu, Shang-Fan,Lau, Jeff,Li, Guangmin,Phillips, Gail D.,Leipold, Doug,Kamath, Amrita,Su, Dian,Xu, Keyang,Eigenbrot, Charles,Steinbacher, Stefan,Ohri, Rachana,Raab, Helga,Staben, Leanna R.,Zhao, Guiling,Flygare, John A.,Pillow, Thomas H.,Verma, Vishal,Masterson, Luke A.,Howard, Philip W.,Safina, Brian. "Discovery of Peptidomimetic Antibody-Drug Conjugate Linkers with Enhanced Protease Specificity". supporting information. p. 989 - 1000. Retrieved 2018/01/01.