Z-TYR(BZL)-OH

Base Information

• Chemical Name: Z-TYR(BZL)-OH
• CAS No.: 16677-29-5
• Molecular Formula: C₂₄H₂₃NO₅
• Molecular Weight: 405.45
• Mol file: 16677-29-5.mol

Synonyms:Alanine,3-[p-(benzyloxy)phenyl]-N-carboxy-, N-benzyl ester (6CI);Alanine,3-[p-(benzyloxy)phenyl]-N-carboxy-, N-benzyl ester, L- (8CI);N-(Benzyloxycarbonyl)-O-benzyltyrosine;N-Carbobenzoxy-O-benzyl-L-tyrosine;O-Benzyl-N-benzyloxycarbonyl-L-tyrosine;O-Benzyl-N-carbobenzoxy-L-tyrosine;

Chemical Property of Z-TYR(BZL)-OH

Chemical Property:

• Boiling Point: 624.4 °C at 760 mmHg
• PKA: 2.98±0.10(Predicted)
• Flash Point: 331.5 °C
• PSA: 84.86000
• Density: 1.249 g/cm³
• LogP: 4.57860
• Storage Temp.: Store at 0°C

Purity/Quality:

99%, ^*data from raw suppliers

Z-Tyr(Bzl)-OH 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Z-TYR(BZL)-OH

There total 6 articles about Z-TYR(BZL)-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: 95.0%

O-benzyl-S-tyrosine (16652-64-5) + benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonyl-O-benzyl-L-tyrosine (86827-18-1,92455-53-3,16677-29-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 2h;

DOI:10.1016/j.tet.2014.05.098

Reference yield: 72.0%

N-benzyloxycarbonyl-O-benzyl-L-tyrosine benzyl ester (315203-50-0) → N-benzyloxycarbonyl-O-benzyl-L-tyrosine (86827-18-1,92455-53-3,16677-29-5)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogen; palladium on activated charcoal; ethylenediamine; In methanol; ethyl acetate; at 20 ℃; for 24h; under 760 Torr;

DOI:10.1016/S0040-4020(00)00771-7

Reference yield: 58.0%

Z-L-Tyr-OH (1164-16-5) + benzyl bromide (100-39-0) → N-benzyloxycarbonyl-O-benzyl-L-tyrosine (86827-18-1,92455-53-3,16677-29-5)

Guidance literature:

Z-L-Tyr-OH; With sodium methylate; In methanol; at 20 ℃; for 0.25h; Cooling with ice;

benzyl bromide; In methanol; at 20 ℃;

DOI:10.1016/j.bmcl.2016.09.001

upstream raw materials:

O-benzyl-S-tyrosine

benzyl chloroformate

N-benzyloxycarbonyl-O-benzyl-L-tyrosine benzyl ester

benzyl bromide

Downstream raw materials:

Z-Tyr(OBzl)-ONp

Z-Tyr(OBzl)-ONB

N-benzyloxycarbonyl-O-benzyl-(S)tyrosyl-glycine methyl ester

Z-Tyr(Bzl)-OTAP

Refernces

• 1、 Zheng, Yongpeng,Xu, Jiaxi. "Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids". . p. 5197 - 5206. Retrieved 2014/07/08.
• 2、 Hattori, Kazuyuki,Sajiki, Hironao,Hirota, Kosaku. "Pd/C(en)-catalyzed chemoselective hydrogenation with retention of the N-Cbz protective group and its scope and limitations". . p. 8433 - 8441. Retrieved 2007/10/03.