Z-Tyr(tbu)-OH

Base Information

• Chemical Name: Z-Tyr(tbu)-OH
• CAS No.: 5545-54-0
• Molecular Formula: C21H25NO5
• Molecular Weight: 371.433
• European Community (EC) Number: 611-269-4
• DSSTox Substance ID: DTXSID20359663
• Nikkaji Number: J365.232G
• Wikidata: Q72470439
• Mol file: 5545-54-0.mol

Synonyms:Z-TYR(TBU)-OH;5545-54-0;(S)-2-(((Benzyloxy)carbonyl)amino)-3-(4-(tert-butoxy)phenyl)propanoic acid;N-Cbz-O-(tert-butyl)-L-tyrosine;(2S)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoic acid;L-Tyrosine, O-(1,1-dimethylethyl)-N-[(phenylmethoxy)carbonyl]-;MFCD00065701;Z-Tyr(But)-OH;Z-Tyr(t-Bu)-OH;SCHEMBL630884;DTXSID20359663;AC8096;AKOS016014751;DS-6840;N-benzyloxycarbonyl-O-t-butyl-l-tyrosine;O-tert-Butyl-N-(benzyloxycarbonyl)tyrosine;CS-0187718;EN300-7372313;N-(benzyloxycarbonyl)-3-(4-tert.butoxyphenyl)-L-alanine;N-(benzyloxycarbonyl)-O-(1,1-dimethylethyl)-L-tyrosine;(S)-2-(benzyloxycarbonylamino)-3-(4-tert-butoxyphenyl)propanoic acid;(2S)-2-{[(BENZYLOXY)CARBONYL]AMINO}-3-[4-(TERT-BUTOXY)PHENYL]PROPANOIC ACID

Chemical Property of Z-Tyr(tbu)-OH

Chemical Property:

• Melting Point: 73-79°C
• Boiling Point: 556.8±50.0 °C(Predicted)
• PKA: 2.99±0.10(Predicted)
• PSA: 88.35000
• Density: 1.185±0.06 g/cm3(Predicted)
• LogP: 3.99040
• Storage Temp.: Store at 0-5°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 371.17327290
• Heavy Atom Count: 27
• Complexity: 474

Purity/Quality:

98%Min ^*data from raw suppliers

Z-Tyr(tBu)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC1=CC=C(C=C1)CC(C(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)OCC2=CC=CC=C2

Technology Process of Z-Tyr(tbu)-OH

There total 13 articles about Z-Tyr(tbu)-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: 89.7%

N-(benzyloxycarbonyl)-O-tert-butyltyrosine ethyl ester (66328-78-7) → N-(benzyloxycarbonyl)-O-(1,1-dimethylethyl)-L-tyrosine (5545-54-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/jm00390a005

Reference yield:

N-(benzyloxycarbonyl)-L-tyrosine methyl ester (13512-31-7) + isobutene (115-11-7,15220-85-6) → N-(benzyloxycarbonyl)-O-(1,1-dimethylethyl)-L-tyrosine (5545-54-0)

Guidance literature:

With sulfuric acid; In dichloromethane; at 20 ℃; for 120h;

Reference yield:

N-[(phenylmethoxy)carbonyl]-L-tyrosine (16679-94-0) → N-(benzyloxycarbonyl)-O-(1,1-dimethylethyl)-L-tyrosine (5545-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: conc. H₂SO₄ / CH₂Cl₂

2: 89.7 percent / 0.25 N NaOH / tetrahydrofuran / 25 °C

With sodium hydroxide; sulfuric acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00390a005

upstream raw materials:

N-Benzyloxycarbonyl-O-tert.-butyl-L-tyrosin-(4-nitro-benzylester)

N-(benzyloxycarbonyl)-O-tert-butyltyrosine ethyl ester

2-benzyloxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionic acid methyl ester

N-(benzyloxycarbonyl)-L-tyrosine methyl ester

Downstream raw materials:

N-Z-O-tert-butyl-L-tyrosine pentachlorophenyl ester

N-(benzyloxycarbonyl)-O-tert-butyltyrosylglycylglycine ethyl ester

Z-Tyr(Bu^t)-Gly-OPh

N-benzyloxycarbonyl-O-t-butyl-L-tyrosyl-α-aminoisobutyric acid methyl ester

Refernces

• 1、 Caplar, Vesna,Raza, Zlata,Katalenic, Darinka,Zinic, Mladen. "Syntheses of amino alcohols and chiral C2-symmetric bisoxazolines derived from O-alkylated R-4-hydroxyphenylglycine and S-tyrosine". . p. 23 - 36. Retrieved 2007/10/03.