Z-D-NLE-OH

Base Information

• Chemical Name: Z-D-NLE-OH
• CAS No.: 15027-14-2
• Molecular Formula: C14H19NO4
• Molecular Weight: 265.309
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID20426480
• Nikkaji Number: J58.656K
• Wikidata: Q72442060
• Mol file: 15027-14-2.mol

Synonyms:D-(Carbobenzyloxy)norleucine;Z-D-Nle-OH;Norleucine,N-carboxy-, N-benzyl ester, D- (8CI);

Chemical Property of Z-D-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
• PKA: 4.00±0.21(Predicted)
• 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-D-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-D-NLE-OH

There total 14 articles about Z-D-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: 90.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + D-norleucine (327-56-0) → (R)-(((benzyloxy)carbonyl)amino)-D-norleucine (15027-14-2)

Guidance literature:

With sodium hydrogencarbonate; sodium carbonate; In water; acetone; at 20 ℃; for 12h;

DOI:10.1021/acs.joc.5b01292

Reference yield: 87.0%

ethanol (64-17-5) + N-benzyloxycarbonylnorleucine (15027-13-1) → (R)-(((benzyloxy)carbonyl)amino)-D-norleucine (15027-14-2) + L-Z-Nor-Leu-OEt (117402-84-3,126401-01-2)

Guidance literature:

With citrate buffer; DL-cysteine hydrochloride; papain; at 50 ℃; for 24h;

Reference yield: 82.0%

benzyl-((3R)-1,2-dihydroxyheptan-3-yl)carbamate → (R)-(((benzyloxy)carbonyl)amino)-D-norleucine (15027-14-2)

Guidance literature:

benzyl-((3R)-1,2-dihydroxyheptan-3-yl)carbamate; With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 2h; Inert atmosphere;

With sodium chlorite; sodium dihydrogenphosphate; In tetrahydrofuran; water; tert-butyl alcohol; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1002/chem.202002449

upstream raw materials:

ethanol

N-benzyloxycarbonylnorleucine

2-amino-hexanoic acid

benzyl chloroformate

Downstream raw materials:

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

Boc-Nle-gGly-D-Trp-D-Nle-Z

2-D-Norleucyl-L-norleucin

2-D-Norleucyl-L-norleucin-methylester

Refernces

• 1、 Wang, Shuni,Zhou, Shengbin,Wang, Jiang,Nian, Yong,Kawashima, Aki,Moriwaki, Hiroki,Ace?a, José L.,Soloshonok, Vadim A.,Liu, Hong. "Chemical Dynamic Thermodynamic Resolution and S/R Interconversion of Unprotected Unnatural Tailor-made α-Amino Acids". . p. 9817 - 9830. Retrieved 2015/11/03.
• 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.