Z-TYR(TBU)-OET

Base Information

• Chemical Name: Z-TYR(TBU)-OET
• CAS No.: 66328-78-7
• Molecular Formula: C23H29 N O5
• Molecular Weight: 399.487
• Mol file: 66328-78-7.mol

Synonyms:Alanine, 3-(p-tert-butoxyphenyl)-N-carboxy-, N-benzyl ethyl ester (7CI)

Chemical Property of Z-TYR(TBU)-OET

Chemical Property:

• PSA: 73.86000
• LogP: 4.65540

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Z-TYR(TBU)-OET

There total 1 articles about Z-TYR(TBU)-OET 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:

N-[(phenylmethoxy)carbonyl]-L-tyrosine (16679-94-0) + isobutene (115-11-7,15220-85-6) → N-(benzyloxycarbonyl)-O-tert-butyltyrosine ethyl ester (66328-78-7)

Guidance literature:

With sulfuric acid; In dichloromethane;

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)-O-tert-butyltyrosine ethyl ester (66328-78-7) → (N,N-dipropyl,Leu5)enkephalin (107941-77-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 89.7 percent / 0.25 N NaOH / tetrahydrofuran / 25 °C

2: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, 2.) THF, DMF

3: 80.7 percent / 0.25 N NaOH / tetrahydrofuran

4: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, 2.) THF, DMF

5: 91.9 percent / ammonium formate, H₂ / 10percent Pd/C / methanol / 0.67 h

6: 43.3 percent / N,N-diisopropylethylamine / toluene / 6.5 h / Heating

7: 78.7 percent / 0.25 N NaOH / tetrahydrofuran / 7.5 h / 25 °C

8: 68.4 percent / 50percent CF₃COOH, 10percent anisole / CH₂Cl₂ / 2.5 h / 25 °C

With 4-methyl-morpholine; sodium hydroxide; hydrogen; ammonium formate; methoxybenzene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/jm00390a005

upstream raw materials:

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

isobutene

Downstream raw materials:

N-(benzyloxycarbonyl)-O-(1,1-dimethylethyl)-L-tyrosine

O-tert.-Butyl-L-tyrosinaethylester

Z-L-Tyr(Bu-t)-Gly-Gly-OH

O-tert-butyltyrosylglycylglycine ethyl ester

Refernces