87553-74-0

Basic information

• Product Name: H-D-TYR-OTBU
• Synonyms: D-TYROSINE-T-BUTYL ESTER;D-TYROSINE-OTBU;H-D-TYR-OTBU;D-Tyr-OtBu
• CAS NO: 87553-74-0
• Molecular Formula: C13H19NO3
• Molecular Weight: 237.29
• Product Categories: Amino Acids and Derivatives;Amino Acid Derivatives
• Mol File: 87553-74-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 142-143℃
• Boiling Point: 358.1 °C at 760 mmHg
• Flash Point: 170.4 °C
• Appearance: /Solid
• Density: 1.125
• Vapor Pressure: 1.26E-05mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: 2-8°C
• PKA: 9.80±0.15(Predicted)
• Water Solubility: Very slightly soluble in cold water.
• CAS DataBase Reference: H-D-TYR-OTBU(CAS DataBase Reference)
• NIST Chemistry Reference: H-D-TYR-OTBU(87553-74-0)
• EPA Substance Registry System: H-D-TYR-OTBU(87553-74-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36-52
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 87553-74-0(Hazardous Substances Data)

Usage

Description

H-D-TYR-OTBU, also known as D-Tyrosine tert-butyl ester, is a protected form of D-Tyrosine (T899970). D-Tyrosine is an unnatural isomer of L-Tyrosine (T899975) that possesses antimetabolic properties and is utilized as a chiral precursor in the synthesis of bioactive compounds.

Uses

Used in Pharmaceutical Industry:
H-D-TYR-OTBU is used as a chiral precursor for the synthesis of bioactive compounds with anti-inflammatory effects in humans. Its role in the development of pharmaceuticals is crucial, as it aids in the creation of inhibitors that can potentially treat various inflammatory conditions.
Used in Microbiology Research:
In the field of microbiology, H-D-TYR-OTBU serves as an antimetabolic agent, specifically inhibiting the metabolic activity of Bacillus subtilis. This application is valuable for studying the effects of antimetabolic substances on bacterial growth and development, furthering our understanding of microbial physiology and potential antimicrobial strategies.
Used in Nutritional and Metabolic Studies:
H-D-TYR-OTBU is utilized in nutritional and metabolic research on rats, where it has been observed to inhibit growth and development. This application is instrumental in exploring the impacts of D-amino acids on animal metabolism and growth, providing insights into the broader implications of amino acid stereochemistry in biological systems.

InChI:InChI=1/C13H19NO3/c1-13(2,3)17-12(16)11(14)8-9-4-6-10(15)7-5-9/h4-7,11,15H,8,14H2,1-3H3/t11-/m1/s1

Upstream product

• 60-18-4 L-tyrosine 
• 115-11-7 isobutene 
• 16881-33-7 (S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate hydrate 
• 217172-40-2 (S)-2-amino-3-(4-benzyloxy-phenyl)-tert-butyl-propionic ester 
• 5544-60-5 4-(benzyloxy)benzyl bromide 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 1027921-22-7 2-(benzhydrylidene-amino)-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester 
• 1164-16-5 Z-L-Tyr-OH 
• 540-88-5 acetic acid tert-butyl ester 
• 88878-78-8 tyrosine tert-butyl ester 
• 67-56-1 methanol 
• 112883-29-1 N-Fmoc-Tyr-OH 
• 133852-23-0 tert-butyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate 
• 556-02-5 ?Tyr 

Downstream Products

• 179188-06-8 N-benzyltyrosine tert-butyl ester 
• 192822-99-4 N,N-dibenzyltyrosine tert-butyl ester 
• 216502-61-3 (S)-3-(4-Hydroxy-3-nitro-phenyl)-2-(2,2,2-trifluoro-acetylamino)-propionic acid tert-butyl ester 
• 142822-21-7 L-seryl-L-tyrosine tert-butyl ester 
• 142822-22-8 L-pyroglutamyl-L-histidyl-L-trypthophyl-L-seryl-L-tyrosine tert-butyl ester 
• 1279713-95-9 (S)-2-(benzo[b]thiophene-2-carboxamido)-3-(4-hydroxyphenyl)propanoic acid 
• 1279713-82-4 (R)-2-(benzo[b]thiophene-2-carboxamido)-3-(4-hydroxyphenyl)propanoic acid 
• 1279713-93-7 (S)-2-(3-chloro-6-fluorobenzo[b]thiophene-2-carboxamido)-3-(4-hydroxyphenyl)propanoic acid 
• 1352734-68-9 (2S)-2-(2-(5-(5-((Z)-(3-(bicyclo[2.2.1]heptan-2-yl)-4-oxo-2-thioxothiazolidin-5-ylidene)methyl)furan-2-yl)-2-methoxyphenoxy)acetamido)-3-(4-hydroxyphenyl)propanoic acid 
• 75768-66-0 L-N-(benzyl)-tyrosine 

Relevant articles and documents

Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids

We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.

A Bioinspired Synthesis of Polyfunctional Indoles

Polyfunctional indoles bearing substituents at C5 and C6 are prevalent in natural products, pharmaceuticals, agrochemicals, and materials. Owing to the remoteness of the C5 and C6 positions, indoles of this family can be difficult to prepare, and often require multistep syntheses. Herein, we describe a concise process that converts simple derivatives of tyrosine into 5,6-difunctionalized indoles by direct oxidation of C?H, N?H, and O?H bonds. Our work draws inspiration from the biosynthetic polymerization of tyrosine to make melanin pigments, but makes an important departure to provide well-defined indole heterocycles.

A novel SWCNT platform bearing DOTA and β-cyclodextrin units. "one shot" multidecoration under microwave irradiation

The functionalization of single-walled carbon nanotubes (SWCNTs) via microwave-assisted grafting reactions enables efficient multidecoration in a single step. A novel water-soluble SWCNT platform was prepared via the simple 1,3-dipolar cycloaddition of azomethine ylides under dielectric heating. Thanks to a single grafting reaction the CNT surface binds in a 1:1 ratio an amino acidic β-cyclodextrin (β-CD) derivative and the DOTAMA moiety (1,4,7,10-tetraazacyclododecane-N,N′,N′′,N′′ ′-tetraacetic acid monoamide). This novel "one shot" synthesis, compared with multistep functionalizations, preserves the SWCNT's structural integrity (TEM images). Besides thermogravimetric analyses, the determination of the amount of β-CD and DOTA moieties grafting onto the SWCNT's surface was performed on the basis of phenolphthalein and gadolinium complexation, respectively. This journal is