99953-00-1

Basic information

• Product Name: L-TYROSINE, N[(1,1-DIMETHYLETHOXY) CARBONYL] -2,6
• Synonyms: N-Boc-2,6-Dimethyl-L-tyrosine;(S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoic acid;N-Boc-2,6-DiMethyl-L-tyrosine/(S)-2-(tert-butoxycarbonylaMino)-3-(4-hydroxy-2,6-diMethylphenyl)propanoic acid;2-(tert-butoxycarbonylamino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoic acid;N-tert-Butoxycarbonyl-2,6-dimethyl-L-tyrosine;Boc-2,6-dimethyl-L-tyrosine;-3-(4-hydroxy-2,6-dimethylphenyl)
• CAS NO: 99953-00-1
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.36
• Mol File: 99953-00-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 174-177 °C
• Boiling Point: 512.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.191±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.06±0.10(Predicted)
• CAS DataBase Reference: L-TYROSINE, N[(1,1-DIMETHYLETHOXY) CARBONYL] -2,6(CAS DataBase Reference)
• NIST Chemistry Reference: L-TYROSINE, N[(1,1-DIMETHYLETHOXY) CARBONYL] -2,6(99953-00-1)
• EPA Substance Registry System: L-TYROSINE, N[(1,1-DIMETHYLETHOXY) CARBONYL] -2,6(99953-00-1)

Safety Data

• Hazardous Substances Data: 99953-00-1(Hazardous Substances Data)

Usage

General Description

L-Tyrosine, N[(1,1-dimethylethoxy) carbonyl]-2,6 is a chemical compound that is derived from the amino acid tyrosine. It is commonly used as a supplement to support brain health and cognitive function. L-Tyrosine plays a key role in the production of neurotransmitters such as dopamine, adrenaline, and noradrenaline. The addition of the N[(1,1-dimethylethoxy) carbonyl]-2,6 group to the tyrosine molecule helps to improve its stability and bioavailability. L-TYROSINE, N[(1,1-DIMETHYLETHOXY) CARBONYL] -2,6 is often used in nootropic and athletic performance supplements to enhance mental focus, concentration, and overall cognitive performance.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 123715-02-6 H-Dmt 
• 1255098-61-3 N-acetyl-2,6-dimethyl-DL-tyrosine 
• 1333148-31-4 (S)-N-acetyl-2,6-dimethyltyrosine 
• 145235-86-5 (S)-4-acetoxy-N-acetyl-2,6-dimethylphenylalanine methyl ester 
• 80826-86-4 4-iodo-3,5-dimethylphenol 
• 145235-84-3 4-iodo-3,5-dimethylphenyl acetate 
• 145235-85-4 methyl (Z)-2-acetamido-3-(4-acetoxy-2,6-dimethylphenyl)-2-propenoate 
• 108-68-9 3,5-Dimethylphenol 
• 137650-15-8 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoate 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 80110-73-2 2,6-dimethyl-(S)-tyrosine hydrochloride 

Downstream Products

• 137666-07-0 <2,6-dimethyl-Tyr¹,D-Pen²,D-Pen⁵>enkephalin 
• 189093-93-4 Boc-L-Dmt-Tic-OtBu 
• 480446-87-5 {2-[({(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-methyl]-benzoimidazol-1-yl}-acetic acid ethyl ester 
• 480446-78-4 3-(1H-benzoimidazol-2-yl)-3-({2-[2-tert-butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-propionic acid benzyl ester 
• 480446-70-6 3-(1H-benzoimidazol-2-yl)-2-({2-[2-tert-butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-propionic acid benzyl ester 
• 573703-30-7 1-N^α-Boc-Dmt-amino-4-(N^α-Fmoc-Phe-amino)butane 

Relevant articles and documents

2',6'-dimethyltyrosine derivative and C-H activation methylation synthesis method thereof

The present invention provides a 2',6'-dimethyltyrosine derivative and a C-H activation methylation synthesis method thereof, specifically a compound represented by the following formula I, wherein each group is defined in the specification. The invention further provides a preparation method of the compound. The formula I is defined in the specification.

Rapid Synthesis of Boc-2′,6′-dimethyl- l -tyrosine and Derivatives and Incorporation into Opioid Peptidomimetics

The unnatural amino acid 2′,6′-dimethyl-l-tyrosine has found widespread use in the development of synthetic opioid ligands. Opioids featuring this residue at the N-terminus often display superior potency at one or more of the opioid receptor types, but the availability of the compound is hampered by its cost and difficult synthesis. We report here a short, three-step synthesis of Boc-2′,6′-dimethyl-l-tyrosine (3a) utilizing a microwave-assisted Negishi coupling for the key carbon-carbon bond forming step, and employ this chemistry for the expedient synthesis of other unnatural tyrosine derivatives. Three of these derivatives (3c, 3d, 3f) have not previously been examined as Tyr1 replacements in opioid ligands. We describe the incorporation of these tyrosine derivatives in a series of opioid peptidomimetics employing our previously reported tetrahydroquinoline (THQ) scaffold, and the binding and relative efficacy of each of the analogues at the three opioid receptor subtypes: mu (MOR), delta (DOR), and kappa (KOR).

Studies on the structure-activity relationship of 2′,6′- dimethyl-l-tyrosine (Dmt) derivatives: Bioactivity profile of H-Dmt-NH-CH 3

The 2′,6′-dimethyl-l-tyrosine (Dmt) enhances receptor affinity, functional bioactivity and in vivo analgesia of opioid peptides. To further investigate its direct influence on these opioid parameters, we developed a series of compounds (H-Dmt-NH-X). Among them, H-Dmt-NH-CH3 showed the highest affinity (Kiμ = 7.45 nM) equal to that of morphine, partial μ-opioid agonism (Emax = 66.6%) in vitro and a moderate antinociception in mice.