N-Benzyloxycarbonyl-L-isoleucine

Base Information

• Chemical Name: N-Benzyloxycarbonyl-L-isoleucine
• CAS No.: 3160-59-6
• Molecular Formula: C14H19NO4
• Molecular Weight: 265.309
• Hs Code.: 29242990
• European Community (EC) Number: 221-611-0
• DSSTox Substance ID: DTXSID80953565
• Mol file: 3160-59-6.mol

Synonyms:2-(((Benzyloxy)carbonyl)amino)-3-methylpentanoic acid;2-{[(benzyloxy)carbonyl]amino}-3-methylpentanoic acid;N-Benzyloxycarbonyl-L-isoleucine;Cbz-D-Ile-OH;N-benzyl-oxycarbonylisoleucine;3-methyl-2-(phenylmethoxycarbonylamino)pentanoic acid;SCHEMBL5145628;DTXSID80953565;N-benzyloxycarbonyl-DL-isoleucine;Isoleucine, N-carboxy-, N-benzyl ester, D- (8CI);N-(Benzyloxycarbonyl)-D-isoleucine;JSHXJPFZKBRLFU-UHFFFAOYSA-N;EINECS 221-611-0;MFCD02094394;AKOS000120791;AKOS016890701;AB25150;NCGC00330439-01;SY026339;CS-0058407;FT-0634710;FT-0698594;EN300-20813;N-[(Benzyloxy)(hydroxy)methylidene]isoleucine;AB01335030-01;Z104483014

Chemical Property of N-Benzyloxycarbonyl-L-isoleucine

Chemical Property:

• Appearance/Colour: white to yellowish weak solid
• Vapor Pressure: 1.28E-08mmHg at 25°C
• Melting Point: 52-54 °C(lit.)
• Refractive Index: 6.5 ° (C=6, EtOH)
• Boiling Point: 442.8 °C at 760 mmHg
• PKA: 4.02±0.22(Predicted)
• Flash Point: 221.6 °C
• PSA: 75.63000
• Density: 1.158 g/cm³
• LogP: 2.80300
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Ethanol (Sparingly), Methanol (Sparingly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 265.13140809
• Heavy Atom Count: 19
• Complexity: 300

Purity/Quality:

99.9% ^*data from raw suppliers

Z-L-isoleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)O)NC(=O)OCC1=CC=CC=C1

Technology Process of N-Benzyloxycarbonyl-L-isoleucine

There total 50 articles about N-Benzyloxycarbonyl-L-isoleucine 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: 87.0%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) + O-benzyl S-(pyridin-2-yl)carbonothioate (91285-94-8) → N-Cbz-L-Isoleucine (3160-59-6)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 0.5h; Ambient temperature;

DOI:10.1246/bcsj.58.3570

Reference yield: 86.0%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) + benzyl pyridin-2-yl carbonate (96452-48-1) → N-Cbz-L-Isoleucine (3160-59-6)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 0.5h; Ambient temperature;

DOI:10.1246/bcsj.58.3570

Reference yield: 85.0%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) + dimethylsulfonium methyl sulfate → N-Cbz-L-Isoleucine (3160-59-6)

Guidance literature:

With triethylamine; In water; Ambient temperature;

DOI:10.1246/bcsj.62.3103

upstream raw materials:

isoleucine

benzyl chloroformate

C₉H₉NO₂C₂H₃CHC

L-ZIleONp

Downstream raw materials:

N-Benzyloxycarbonyl-L-isoleucyl-L-leucin

N-(N-benzyloxycarbonyl-L-isoleucyl)-L-tyrosine benzyl ester

N-(N-benzyloxycarbonyl-D-alloisoleucyl)-D-alanine benzyl ester

Z-Ile-His-OMe

Refernces

• 1、 Dola, Vasantha Rao,Soni, Awakash,Agarwal, Pooja,Ahmad, Hafsa,Raju, Kanumuri Siva Rama,Rashid, Mamunur,Wahajuddin, Muhammad,Srivastava, Kumkum,Haq,Dwivedi,Puri,Katti. "Synthesis and evaluation of chirally defined side chain variants of 7-chloro-4-aminoquinoline to overcome drug resistance in malaria chemotherapy". . . Retrieved 2017/03/09.
• 2、 Thanigaimalai, Pillaiyar,Konno, Sho,Yamamoto, Takehito,Koiwai, Yuji,Taguchi, Akihiro,Takayama, Kentaro,Yakushiji, Fumika,Akaji, Kenichi,Kiso, Yoshiaki,Kawasaki, Yuko,Chen, Shen-En,Naser-Tavakolian, Aurash,Sch?n, Arne,Freire, Ernesto,Hayashi, Yoshio. "Design, synthesis, and biological evaluation of novel dipeptide-type SARS-CoV 3CL protease inhibitors: Structure-activity relationship study". . p. 436 - 447. Retrieved 2013/10/01.