Cbz-L-Tyrosine benzyl ester

Base Information

• Chemical Name: Cbz-L-Tyrosine benzyl ester
• CAS No.: 5513-40-6
• Molecular Formula: C24H23 N O5
• Molecular Weight: 405.45
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID60426722
• Nikkaji Number: J276.768F
• Wikidata: Q82239549
• Mol file: 5513-40-6.mol

Synonyms:5513-40-6;Cbz-L-Tyrosine benzyl ester;Z-TYR-OBZL;(S)-Benzyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate;Benzyl ((benzyloxy)carbonyl)-L-tyrosinate;Nalpha-Carbobenzoxy-L-tyrosine-benzyl ester;benzyl (2S)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoate;(S)-Benzyl 2-(benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propanoate;Cbz-Tyr-Obzl;Z-L-Tyrosine benzyl ester;Z-L-Tyrosine-benzyl ester;SCHEMBL3065366;DTXSID60426722;L-Tyrosine, N-[(phenylmethoxy)carbonyl]-, phenylmethyl ester;MFCD00136670;AKOS015839310;AKOS015888548;DS-3619;n-carbobenzyloxy-l-tyrosine benzyl ester;AM20040701;CS-0149875;L-Tyrosine,N-[(phenylmethoxy)carbonyl]-,phenylmethyl ester;(2S)-2-(Benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propionic acid benzyl ester

Chemical Property of Cbz-L-Tyrosine benzyl ester

Chemical Property:

• Boiling Point: 610.8±55.0 °C(Predicted)
• PKA: 9.74±0.15(Predicted)
• PSA: 84.86000
• Density: 1.250±0.06 g/cm3(Predicted)
• LogP: 4.36400
• Storage Temp.: Room temperature.
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 405.15762283
• Heavy Atom Count: 30
• Complexity: 520

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cbz-L-Tyrosinebenzylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C(CC2=CC=C(C=C2)O)NC(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)OCC3=CC=CC=C3

Technology Process of Cbz-L-Tyrosine benzyl ester

There total 12 articles about Cbz-L-Tyrosine benzyl ester 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: 95.0%

L-tyrosine benzyl ester p-toluenesulfonate (53587-11-4,97984-63-9) + benzyl chloroformate (501-53-1,94274-21-2) → benzyl N-carbobenzyloxy-L-tyrosine (5513-40-6)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 - 5 ℃; for 4h;

Reference yield: 95.0%

Z-L-Tyr-OH (1164-16-5) + benzyl bromide (100-39-0) → benzyl N-carbobenzyloxy-L-tyrosine (5513-40-6)

Guidance literature:

With caesium carbonate; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(96)01490-6

Reference yield: 76.0%

Z-L-Tyr-OH (1164-16-5) + benzyl alcohol (100-51-6,185532-71-2) → benzyl N-carbobenzyloxy-L-tyrosine (5513-40-6)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 25 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.1c01444

upstream raw materials:

L-tyrosine benzyl ester

benzyl chloroformate

C₂₆H₂₅F₃NO₇P

Z-L-Tyr-OH

Downstream raw materials:

L-N^α-Cbz-4-(O-trifluoromethanesulfonate)tyrosine benzyl ester

C₃₀H₃₈N₃O₆P

(S)-2-Benzyloxycarbonylamino-3-(4-tert-butoxycarbonylmethoxy-phenyl)-propionic acid benzyl ester

(S)-2-Benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propionic acid benzyl ester

Refernces

• 1、 Baygildiev, T. M.,Krylov, I. I.,Krylov, V. I.,Osipov, V. N.,Rodin, I. A.,Rybalchenko, I. V.,Yashkir, V. A.. "Phosphorylation of Tyrosine and Tyr-Thr-Lys Tripeptide with Cyclohexylmethyl- and (Deuteromethyl)phosphonochloridates". . p. 619 - 623. Retrieved 2020/07/02.
• 2、 Sato, Atsushi,Yoshida, Masanori,Hara, Shoji. "Primary amino acid lithium salt as a catalyst for asymmetric Michael addition of isobutyraldehyde with β-nitroalkenes". supporting information; experimental part. p. 6242 - 6244. Retrieved 2009/05/06.