Z-Nle-OH

Base Information

• Chemical Name: Z-Nle-OH
• CAS No.: 39608-30-5
• Molecular Formula: C14H19NO4
• Molecular Weight: 265.309
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID70426354
• Nikkaji Number: J58.655B
• Wikidata: Q72502198
• ChEMBL ID: CHEMBL4990381
• Mol file: 39608-30-5.mol

Synonyms:Z-Nle-OH;39608-30-5;Z-L-Norleucine;Cbz-L-norleucine;(2S)-2-(phenylmethoxycarbonylamino)hexanoic acid;Z-L-2-aminohexanoic acid;Z-norLeu-OH;Cbz-Nle-OH;N-Cbz-L-norleucine;MFCD00063170;Z-L-Nle;SCHEMBL4126228;N-benzyloxycarbonyl-L-norleucine;CHEMBL4990381;DTXSID70426354;NMYWMOZOCYAHNC-LBPRGKRZSA-N;N-(Benzyloxycarbonyl)-L-norleucine;Z-Nle-OH, >=98.0%;AKOS015911505;AM82592;HY-W142039;AS-76084;norleucine, N-[(phenylmethoxy)carbonyl]-;TS-03875;CS-0201824;F78655;EN300-6747400;(2s)-2-{[(benzyloxy)carbonyl]amino}hexanoic acid;(S)-2-(((Benzyloxy)carbonyl)amino)hexanoic acid

Chemical Property of Z-Nle-OH

Chemical Property:

• Vapor Pressure: 7.43E-09mmHg at 25°C
• Melting Point: 56-58 °C
• Refractive Index: 1.528
• Boiling Point: 449.208 °C at 760 mmHg
• Flash Point: 225.473 °C
• PSA: 75.63000
• Density: 1.161 g/cm³
• LogP: 2.94710
• Storage Temp.: Store at RT.
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 265.13140809
• Heavy Atom Count: 19
• Complexity: 287

Purity/Quality:

99% ^*data from raw suppliers

Z-L-norleucine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Z-Nle-OH

There total 13 articles about Z-Nle-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:

methyl-2-(S)-2-(benzyloxycarbonylamino)-2-hexanoate (67675-32-5) → N-benzyloxycarbonyl-L-norleucine (39608-30-5)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2012.11.026

Reference yield:

(R/S)-N-benzyloxycarbonyl-1-phenylhept-1-en-3-ylamine → N-benzyloxycarbonyl-L-norleucine (39608-30-5) + (R)-(((benzyloxy)carbonyl)amino)-D-norleucine (15027-14-2)

Guidance literature:

With ruthenium trichloride; periodic acid; In tetrachloromethane; water; acetonitrile; at 50 ℃; for 24h; Title compound not separated from byproducts;

DOI:10.1021/jo9901079

Reference yield:

2-Benzyloxycarbonylamino-hexanoic acid 2,2,2-trifluoro-ethyl ester (127862-68-4) → (R)-2-Benzyloxycarbonylamino-hexanoic acid (15027-13-1,15027-14-2,39608-30-5)

Guidance literature:

With sodium hydroxide; phosphate buffer; at 25 ℃; for 47h; Yield given. Yields of byproduct given; porcine pancreatic lipase, pH=7.0;

upstream raw materials:

L-Norleucine

N-benzyloxycarbonylnorleucine

N-benzyloxycarbonyl-L-norleucine dicyclohexylamine salt

(S)-2-Benzyloxycarbonylamino-hexanoic acid 4-nitro-benzyl ester

Downstream raw materials:

N-Benzyloxycarbonyl-L-norleucin-2,4,5-trichlorphenylester

Z-Nle-Sar-(Me)Leu-Val-(Me)Leu-Ala-D-Ala-(Me)Leu-(Me)Leu-(Me)Val-Ot-Bu

((S)-2-Benzyloxycarbonylamino-hexanoylsulfamoyl)-acetic acid ethyl ester

Boc-Tyr-Nle-Gly-Trp-OH

Refernces

• 1、 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.
• 2、 Moody, Christopher J.,Lightfoot, Andrew P.,Gallagher, Peter T.. "Addition of Organolithiums to the (R)-O-(1-Phenylbutyl)hydroxylamine (ROPHy) Oxime of Cinnamaldehyde. Asymmetric Synthesis of α-Aminoacids". . p. 659 - 660. Retrieved 2007/10/03.