N-(N-((Phenylmethoxy)carbonyl)-L-isoleucyl)glycine

Base Information

• Chemical Name: N-(N-((Phenylmethoxy)carbonyl)-L-isoleucyl)glycine
• CAS No.: 13254-04-1
• Molecular Formula: C16H22 N2 O5
• Molecular Weight: 322.361
• European Community (EC) Number: 236-241-5
• DSSTox Substance ID: DTXSID90927717
• Nikkaji Number: J213.782H
• Wikidata: Q82902362
• Mol file: 13254-04-1.mol

Synonyms:13254-04-1;Z-ILE-GLY-OH;N-(N-((Phenylmethoxy)carbonyl)-L-isoleucyl)glycine;Glycine, N-[(phenylmethoxy)carbonyl]-L-isoleucyl-;2-[[(2S,3S)-3-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]acetic acid;EINECS 236-241-5;N-[N-[(Phenylmethoxy)carbonyl]-L-isoleucyl]glycine;Z-Ile-Gly;DTXSID90927717;A1-03689;2-((2S,3S)-2-(benzyloxycarbonylamino)-3-methylpentanamido)acetic acid;N-(2-{[(Benzyloxy)(hydroxy)methylidene]amino}-1-hydroxy-3-methylpentylidene)glycine

Chemical Property of N-(N-((Phenylmethoxy)carbonyl)-L-isoleucyl)glycine

Chemical Property:

• Vapor Pressure: 2.17E-14mmHg at 25°C
• Boiling Point: 582°Cat760mmHg
• Flash Point: 305.8°C
• PSA: 104.73000
• Density: 1.203g/cm³
• LogP: 2.31010
• Storage Temp.: -15°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 322.15287181
• Heavy Atom Count: 23
• Complexity: 407

Purity/Quality:

99% ^*data from raw suppliers

Glycine N-[(phenylmethoxy)carbonyl]-L-isoleucyl-95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)NCC(=O)O)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)NCC(=O)O)NC(=O)OCC1=CC=CC=C1

Technology Process of N-(N-((Phenylmethoxy)carbonyl)-L-isoleucyl)glycine

There total 9 articles about N-(N-((Phenylmethoxy)carbonyl)-L-isoleucyl)glycine 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:

methyl 2-(2-(((benzyloxy)carbonyl)amino)-3-methylpentanamido)acetate (2280-67-3) → N-Z-Isoleucin-Glycin (13254-04-1)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja01048a057

Reference yield:

(2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoic acid; compound with triethyl-amine → N-Z-Isoleucin-Glycin (13254-04-1)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) Ts₂O, HMPA, (ii) /BRN= 635818/, Et₃N

2: aq. NaOH

With sodium hydroxide;

DOI:10.1021/ja01048a057

Reference yield:

Z-L-isoleucine benzotriazole (1072442-07-9) + glycine (56-40-6,18875-39-3,25718-94-9) → N-Z-Isoleucin-Glycin (13254-04-1)

Guidance literature:

With triethylamine; In water; acetonitrile; at 25 ℃; for 2h;

DOI:10.1111/cbdd.12134

upstream raw materials:

N-Z-Ile-Gly-OC(CH₃)3

methyl 2-(2-(((benzyloxy)carbonyl)amino)-3-methylpentanamido)acetate

N-benzyloxycarbonyl-L-isoleucylglycine ethyl ester

N-Cbz-L-Isoleucine

Refernces

• 1、 Crasto, Curtis F.,Forrest, Andrew K.,Karoli, Tomislav,March, Darren R.,Mensah, Lucy,O'Hanlon, Peter J.,Nairn, Michael R.,Oldham, Mark D.,Yue, Weimin,Banwell, Martin G.,Easton, Christopher J.. "Synthesis and activity of analogues of the isoleucyl tRNA synthetase inhibitor SB-203207". . p. 2687 - 2694. Retrieved 2007/10/03.