142847-18-5

Basic information

• Product Name: 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid
• Synonyms: 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid;N-(tert-Butoxycarbonyl)-DL-tyrosine;(Tert-Butoxy)Carbonyl DL-Tyr-OH
• CAS NO: 142847-18-5
• Molecular Formula: C₁₄H₁₉NO₅
• Molecular Weight: 281.30436
• Mol File: 142847-18-5.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 484.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.238±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 2.98±0.10(Predicted)
• CAS DataBase Reference: 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid(142847-18-5)
• EPA Substance Registry System: 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid(142847-18-5)

Safety Data

• Hazardous Substances Data: 142847-18-5(Hazardous Substances Data)

Usage

General Description

The chemical compound 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid, also known as Boc-Tyr-OH, is a derivative of the amino acid tyrosine. It is commonly used in the synthesis of peptides and proteins in the pharmaceutical and biotechnology industries. The compound has a tert-butoxycarbonyl (Boc) protecting group attached to the amino group of the tyrosine residue, allowing for selective deprotection and subsequent peptide synthesis. The hydroxyphenyl group in the molecule also provides potential for binding to specific receptors or enzymes, making it a valuable tool in drug discovery and design.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 2990-25-2 tyrozine hydrochloride 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 556-02-5 ?Tyr 
• 34081-17-9 tyrosine ethyl ester 
• 247088-45-5 (RS)-3-(4-benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 
• 909114-65-4 tert-butyl 4,6-dimethoxy-1,3,5-triazinyl carbonate 
• 89037-64-9 1-tert-butoxycarbonyloxybenzotriazole 

Downstream Products

• 140647-59-2 N-t-butyloxycarbonyl-L-tyrosyl-DL-2-amino-3,3-difluoro-butanoic acid methyl ester 
• 53267-94-0 N-(tert-Butyloxycarbonyl)-O-methyltyrosin-Dicyclohexylammonium-Salz 
• 101998-42-9 N-(tert-Butyloxycarbonyl)-O-isopropyltyrosin-Dicyclohexylammonium-Salz 
• 101998-41-8 N-(tert-Butyloxycarbonyl)-O-ethyltyrosin-Dicyclohexylammonium-Salz 
• 99952-48-4 t-butyloxycarbonyl-tyrosyl-prolinal 
• 94790-24-6 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoate 
• 188576-13-8 methyl 2-[(t-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate 
• 1278586-12-1 Boc-D/L-Tyr(OH)-L-Ala-OMe 
• 1278586-13-2 Boc-D/L-Tyr(OH)-D-Ala-OMe 
• 7635-29-2 O-methyl tyrosine 
• 141895-35-4 2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoic acid 
• 876945-78-7 3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)(methyl)amino)propanoic acid 
• 876945-79-8 tert-butyl (3-(4-(benzyloxy)phenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)(methyl)carbamate 
• 876945-80-1 tert-butyl (1-(4-(benzyloxy)phenyl)-4-(4-methoxyphenyl)-3-oxobutan-2-yl)(methyl)carbamate 

Relevant articles and documents

Naamines and naamidines as novel agents against a plant virus and phytopathogenic fungi

Naamines, naamidines and various derivatives of these marine natural products were synthesized and characterized by means of nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry. The activities of these alkaloids against a plant virus and phytopathogenic fungi were evaluated for the first time. A benzyloxy naamine derivative 15d displayed excellent in vivo activity against tobacco mosaic virus at 500 μg/mL (inactivation activity, 46%; curative activity, 49%; and protective activity, 41%); its activities were higher than the corresponding activities of the commercial plant virucide ribavirin (32%, 35%, and 34%, respectively), making it a promising new lead compound for antiviral research. In vitro assays revealed that the test compounds exhibited very good antifungal activity against 14 kinds of phytopathogenic fungi. Again, the benzyloxy naamine derivative 15d exhibited broad-spectrum fungicidal activity, emerging as a new lead compound for fungicidal research. Additional in vivo assays indicated that many of the compounds displayed inhibitory effects >30%.

Synthesis of l - Epi -capreomycidine derivatives via C-H amination

The l-epi-capreomycidine (Cpm) derivatives were efficiently and stereoselectively synthesized via nitrene C-H insertion starting from a readily available d-Tyr. Design of a substrate that takes into account hydrogen bonding is a critical feature in order

Optimisation of conditions for O-benzyl and N-benzyloxycarbonyl protecting group removal using an automated flow hydrogenator

A versatile, fully automated flow hydrogenator has been developed that is able to perform sequential flow optimisation experiments, flow library hydrogenation, or iterative scale-up hydrogenation. The behaviour of a palladium catalyst in effecting removal of O-benzyl and N-benzyloxycarbonyl protecting groups has been investigated. Significant observations relating to maintaining optimal throughput are reported. A small library of peptidic derivatives has been deprotected in high yield and purity.