N-Benzyloxycarbonyl-L-tyrosine

Base Information

• Chemical Name: N-Benzyloxycarbonyl-L-tyrosine
• CAS No.: 1164-16-5
• Molecular Formula: C17H17NO5
• Molecular Weight: 315.326
• Hs Code.: 29242990
• European Community (EC) Number: 214-609-6
• DSSTox Substance ID: DTXSID301313627
• Nikkaji Number: J80.060K
• Wikidata: Q106902935
• ChEMBL ID: CHEMBL291833
• Mol file: 1164-16-5.mol

Synonyms:N-benzyloxycarbonyl-l-tyrosine;N-cbz-l-Tyr

Chemical Property of N-Benzyloxycarbonyl-L-tyrosine

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 7.21E-14mmHg at 25°C
• Melting Point: 57-60 °C(lit.)
• Refractive Index: 10.0 ° (C=1, AcOH)
• Boiling Point: 570.8 °C at 760 mmHg
• PKA: 2.97±0.10(Predicted)
• Flash Point: 299 °C
• PSA: 95.86000
• Density: 1.323 g/cm³
• LogP: 2.70520
• Storage Temp.: −20°C
• Solubility.: Acetic Acid (Sparingly), DMSO (Slightly), Methanol (Sparingly)
• Water Solubility.: 1.53g/L(25 oC)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 315.11067264
• Heavy Atom Count: 23
• Complexity: 386

Purity/Quality:

99% ^*data from raw suppliers

N-Cbz-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CC2=CC=C(C=C2)O)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)O
• Uses: N-Cbz-L-tyrosine is an N-Cbz-protected form of L-Tyrosine (T899975). L-Tyrosine is an essential amino acid that exhibits in vitro antioxidant and antiradical activities. L-Tyrosine is used as a precursor to synthesize catecholamines (e.g. Norepinephrine HCl [N674500]) in human keratinocytes, and also for the synthesis of proteins and thyroid hormones.

Technology Process of N-Benzyloxycarbonyl-L-tyrosine

There total 36 articles about N-Benzyloxycarbonyl-L-tyrosine 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%

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) + benzyl chloroformate (501-53-1,94274-21-2) → Z-L-Tyr-OH (1164-16-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 4h; Inert atmosphere; Cooling with ice;

DOI:10.1021/ol4031155

Reference yield: 100.0%

N-(benzyloxycarbonyl)-O-(1,1-dimethylethyl)-L-tyrosine (5545-54-0) → Z-L-Tyr-OH (1164-16-5)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; for 0.583333h; Ambient temperature;

DOI:10.1016/S0040-4039(00)79116-7

Reference yield: 100.0%

(S)-1,8-Dioxo-2-aza-spiro[4.5]deca-6,9-diene-2,3-dicarboxylic acid dibenzyl ester (77300-65-3) → Z-L-Tyr-OH (1164-16-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 24h;

upstream raw materials:

N-[(phenylmethoxy)carbonyl]-L-tyrosine

L-tyrosine

benzyl chloroformate

tert-butoxycarbonylglycine p-nitrophenylester

Downstream raw materials:

4-nitrophenyl N-[(benzyloxy)carbonyl]-L-tyrosinate

ZTyrIleOMe

Z-Tyr-Gly-Gly-OEt

N-Benzyloxycarbonyl-L-tyrosin-(4-nitro-benzylester)

Refernces

• 1、 Babi?, Andrej,Vorobiev, Vassily,Xayaphoummine, Céline,Lapicorey, Ga?lle,Chauvin, Anne-Sophie,Helm, Lothar,Allémann, Eric. "Self-Assembled Nanomicelles as MRI Blood-Pool Contrast Agent". . p. 1348 - 1357. Retrieved 2018.
• 2、 Moreno-Cinos, Carlos,Sassetti, Elisa,Salado, Irene G.,Witt, Gesa,Benramdane, Siham,Reinhardt, Laura,Cruz, Cristina D.,Joossens, Jurgen,Van Der Veken, Pieter,Br?tz-Oesterhelt, Heike,Tammela, P?ivi,Winterhalter, Mathias,Gribbon, Philip,Windshügel, Bj?rn,Augustyns, Koen. "α-Amino Diphenyl Phosphonates as Novel Inhibitors of Escherichia coli ClpP Protease". . p. 774 - 797. Retrieved 2019/01/30.