N-(tert-Butoxycarbonyl)-L-tyrosyl-2-methylalanine

Base Information

• Chemical Name: N-(tert-Butoxycarbonyl)-L-tyrosyl-2-methylalanine
• CAS No.: 69872-65-7
• Molecular Formula: C18H26N2O6
• Molecular Weight: 366.414
• DSSTox Substance ID: DTXSID70554388
• Wikidata: Q82435356
• Mol file: 69872-65-7.mol

Synonyms:69872-65-7;N-(tert-Butoxycarbonyl)-L-tyrosyl-2-methylalanine;DTXSID70554388

Chemical Property of N-(tert-Butoxycarbonyl)-L-tyrosyl-2-methylalanine

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 366.17908655
• Heavy Atom Count: 26
• Complexity: 518

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(C)(C)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)NC(C)(C)C(=O)O

Technology Process of N-(tert-Butoxycarbonyl)-L-tyrosyl-2-methylalanine

There total 5 articles about N-(tert-Butoxycarbonyl)-L-tyrosyl-2-methylalanine 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%

N-(tert-butoxycarbonyl)-L-tyrosyl-α-aminoisobutyric acid methyl ester (69872-64-6) → N-(tert-butoxycarbonyl)-L-tyrosyl-α-aminoisobutyric acid (69872-65-7)

Guidance literature:

With sodium hydroxide; In methanol; for 10h;

DOI:10.1002/chem.200500834

Reference yield: 52.0%

2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-2-methyl-propionic acid benzyl ester → N-(tert-butoxycarbonyl)-L-tyrosyl-α-aminoisobutyric acid (69872-65-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 1810.02 Torr;

DOI:10.1021/jm00184a010

Reference yield:

Boc-Tyr-OH (3978-80-1) → N-(tert-butoxycarbonyl)-L-tyrosyl-α-aminoisobutyric acid (69872-65-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / Et₃N, HOBT, DCC / tetrahydrofuran; CHCl₃ / Ambient temperature

2: 90 percent / aq. NaOH / methanol / 0 deg C, 1 h -> room temperature, 4 h

With sodium hydroxide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; chloroform;

DOI:10.1021/jm00397a019

upstream raw materials:

N-(tert-butoxycarbonyl)-L-tyrosyl-α-aminoisobutyric acid methyl ester

Boc-Tyr-OH

di-tert-butyl dicarbonate

L-tyrosine

Downstream raw materials:

N-(tert-butoxycarbonyl)-L-tyrosyl-α-aminoisobutyrylglicine methyl estere

Boc-Tyr-Aib-Tyr-OMe

Boc-Tyr-Aib-Ala-OMe

Boc-Tyr-Aib-Ileu-OMe