37169-36-1

Basic information

• Product Name: (S)-Methyl 2-((tert-butoxycarbonyl)aMino)-3-(3,4-dihydroxyphenyl)propanoate
• Synonyms: (S)-Methyl 2-((tert-butoxycarbonyl)aMino)-3-(3,4-dihydroxyphenyl)propanoate
• CAS NO: 37169-36-1
• Molecular Formula: C₁₅H₂₁NO₆
• Molecular Weight: 311.33034
• Mol File: 37169-36-1.mol

Chemical Properties

• Melting Point: 138 °C(Solv: methanol (67-56-1); water (7732-18-5))
• Boiling Point: 502.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.241±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 9.62±0.20(Predicted)
• CAS DataBase Reference: (S)-Methyl 2-((tert-butoxycarbonyl)aMino)-3-(3,4-dihydroxyphenyl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Methyl 2-((tert-butoxycarbonyl)aMino)-3-(3,4-dihydroxyphenyl)propanoate(37169-36-1)
• EPA Substance Registry System: (S)-Methyl 2-((tert-butoxycarbonyl)aMino)-3-(3,4-dihydroxyphenyl)propanoate(37169-36-1)

Safety Data

• Hazardous Substances Data: 37169-36-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoate is used as a building block for the production of pharmaceuticals and other bioactive compounds. Its structural similarity to naturally occurring amino acids makes it a valuable component in the development of new drugs and pharmaceuticals.
Used in Chemical Research:
(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoate is used as a reagent in chemical research. Its unique structure and properties make it a useful tool for studying various chemical reactions and processes.
Used in Organic Synthesis:
(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoate is used in organic synthesis to create a variety of compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Medicinal Chemistry:
(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoate is used in medicinal chemistry for its potential pharmacological properties. Its structural similarity to naturally occurring amino acids allows it to be used in the development of new drugs and pharmaceuticals with potential therapeutic benefits.

Upstream product

• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 53267-93-9 O-methyl-N-tert-butoxycarbonyl-L-tyrosine 
• 13734-41-3 t-Boc-L-valine 
• 15761-38-3 L-N-Boc-Ala 
• 4530-20-5 BOC-glycine 
• 10332-17-9 Met-OMe 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 2666-93-5 (S)-Leu-OMe 
• 4070-48-8 L-Valine methyl ester 
• 10065-72-2 L-Alanine methyl ester 
• 616-34-2 methoxycarbonylmethylamine 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 7101-51-1 L-DOPA methyl ester 

Downstream Products

• 7101-51-1 L-DOPA methyl ester 
• 1428203-72-8 (R,Z)-tert-butyl 4-((6,7-bis(benzyloxy)-3-((tert-butoxycarbonyl)amino)quinolin-2(1H)-ylidene)amino)-2-hydroxybutanoate 
• 1428203-72-8 (R,E)-tert-butyl 4-((6,7-bis(benzyloxy)-3-((tert-butoxycarbonyl)amino)quinolin-2(1H)-ylidene)amino)-2-hydroxybutanoate 
• 1427521-83-2 (S)-methyl 3-(4,5-bis(benzyloxy)-2-nitrophenyl)-2-((tertbutoxycarbonyl)amino)propanoate 
• 1427521-84-3 (S)-tert-butyl (6,7-bis(benzyloxy)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate 
• 1427521-85-4 (S)-tert-butyl (6,7-bis(benzyloxy)-2-thioxo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate 
• 138908-56-2 (S)-(+)-2-tert-butoxycarbonylamino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester 
• 1607804-01-2 2-(diacetoxyiodo)-1-[(2S)-2-[(di-tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl]-4,5-bis(ethoxymethoxy)benzene 

Relevant articles and documents

Synthesis and antioxidant activity of DOPA peptidomimetics by a novel IBX mediated aromatic oxidative functionalization

DOPA peptidomimetics with stable O-C and N-C covalent bonds between amino acid residues have been prepared by aromatic oxidative functionalization of tyrosine with 2-iodoxybenzoic acid (IBX). The reaction involves the Michael-like nucleophilic addition of

Synthesis and Biological Evaluation of Endocannabinoid Uptake Inhibitors Derived from WOBE437

WOBE437 ((2E,4E)-N-(3,4-dimethoxyphenethyl)dodeca-2,4-dienamide, 1) is a natural product-derived, highly potent inhibitor of endocannabinoid reuptake. In this study, we synthesized almost 80 analogues of 1 with different types of modifications in the dodecadienoyl domain as well as the dimethoxyphenylethyl head group, and we investigated their effects on anandamide uptake into U937 cells. Intriguingly, none of these analogues was a more potent inhibitor of anandamide uptake than WOBE437 (1). At the same time, a number of WOBE437 variants exhibited potencies in the sub-100 nM range, with high selectivity over inhibition of the endocannabinoid-degrading enzyme fatty acid amide hydrolase; two compounds were virtually equipotent with 1. Interestingly, profound activity differences were observed between analogues in which either of the two methoxy substituents in the head group had been replaced by the same bulkier alkoxy group. Some of the compounds described here could be interesting departure points for the development of potent endocannabinoid uptake inhibitors with more drug-like properties.

Structural Transformative Antioxidants for Dual-Responsive Anti-Inflammatory Delivery and Photoacoustic Inflammation Imaging

We have synthesized a PEGylated, phenylboronic acid modified L-DOPA pro-antioxidant (pPAD) that can self-assemble into nanoparticles (pPADN) for the loading of a model glucocorticoid dexamethasone (Dex) through 1,3-diol/phenylboronic acid chemistry and hydrophobic interactions for more effective treatment of inflammation. Upon exposure to ROS, pPADN convert into the active form of L-DOPA, and a cascade of oxidative reactions transform it into antioxidative melanin-like materials. Concomitantly, the structural transformation of pPADN triggers the specific release of Dex, along with the acidic pH of inflammatory tissue. In a rat model of osteoarthritis, Dex-loaded pPADN markedly mitigate synovial inflammation, suppress joint destruction and cartilage matrix degradation, with negligible in vivo toxicity. Moreover, in situ structural transformation makes pPADN suitable for noninvasive monitoring of therapeutic effects as a photoacoustic imaging contrast agent.

Boc-Protection on L-DOPA: an Easy Way to Promote Underwater Adhesion

The ability of mussels to adhere to underwater surfaces has attracted a lot of attention from the scientific community. As proteins containing L-DOPA (3,4-dihydroxyphenyl-l-alanine) are involved in their adhesion, a common strategy to synthesize adhesives

Substituted pyrrole chromone compound or pharmaceutically acceptable salt thereof and preparation method and application thereof

The invention discloses a substituted pyrrole chromone compound or pharmaceutically acceptable salt thereof and a preparation method and application thereof. The structure of the compound or the pharmaceutically acceptable salt thereof is shown in the for

Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused Tetrahydroisoquinolines via Pictet-Spengler Reaction

An enantioselective synthesis of iso-, isothio-, and isoselenohydantoin and diketopiperazine-fused tetrahydroisoquinolines from l-Dopa was reported. The route consists of an Pictet-Spengler reaction of (S)-2-amino-3-(3,4-dimethoxyphenyl)propanoates with v

Crown-ether-modified cyclic dipeptides as supramolecular chiral catalysts

With the objective to develop supramolecular catalysts for useful chemical transformations, we report here a rapid and efficient solid-phase synthesis of novel cyclic dipeptides (crown-CDPs) with a diversity of L-DOPA derived crown ether substituents and

Water-soluble L-DOPA esters

The present invention relates to novel compounds of the formula I, methods for their preparation and their use for treatment of diseases. The invention discloses the synthesis of levodopa (L-DOPA) esters by coupling polyhydroxy compounds or their derivatives to the L-DOPA carboxyl group. The synthesis allows to produce L-DOPA derivatives which are highly soluble in water as well as aqueous and biocompatible liquids and have an improved hydrolytic stability in water or aqueous and biocompatible media for an application over several days. The invention helps producing L-DOPA substances for applications in the fields of medicine, biology and medical engineering as well as in the pharmaceutical industry.

Base/Cryptand/Metal-Free Automated Nucleophilic Radiofluorination of [18F]FDOPA from Iodonium Salts: Importance of Hydrogen Carbonate Counterion

As evidenced by the number of publications and patents published in the last years, the radiosynthesis of 6-[18F]fluoro-3,4-dihydroxy-L-phenylalanine ([18F]FDOPA) using the nucleophilic [18F]F- process remains currently a challenge for the radiochemists scientific community even if promising methods for the radiofluorination of electron-rich aromatic structures were recently developed from arylboronate, arylstannane or iodonium salt precursors. In such context, based on the use of an iodonium triflate salt precursor, we optimized a fast and efficient radiofluorination route fully automated and free from any base, cryptand or metal catalyst for the radiosynthesis of [18F]FDOPA. Using this method, this clinically relevant radiotracer was produced in 64 min, 27–38 % RCY d.c. (n = 5), >99 % RCP, >99 % ee., and high Am 170–230 GBq/μmol. In addition, this optimization study clearly highlighted the important role of a triflate-hydrogen carbonate counterion exchange during the radiolabeling process to achieve high fluorine-18 incorporation yields.

A self-assembled tetrapeptide that acts as a “turn-on” fluorescent sensor for Hg2+ ion

The tetrapeptide (Bz-ΔPhe(p-NPh2)-L-DOPA(protected)-L-Phe-L-Phe-OMe was designed to incorporate seven phenyl rings so that it's conformation, self-assembly and application in Hg2+ ions sensing could be studied. Peptide molecules adopted an overlapping β-turn of type III/III conformation in crystals. The peptide showed a highly selective turn-on response towards mercuric ion over other metal ions with a 10-fold enhancement in fluorescence intensity. This intensity change coupled with the selectivity of the peptide towards mercury allowed us to demonstrate simple colorimetric dip sensing of Hg2+ ions. The technique provides a highly selective and effective way to detect Hg2+ ions. The peptide also self-assembled into nanospheres with diameter ranges from 100 to 500 nm. Mercuric ion coordination enabled these peptide nanospheres to aggregate into well-defined nanoparticles. The enhanced fluorescence upon Hg2+ addition demonstrates that peptide scaffolds can be exploited in the development of different selective sensors.