851967-77-6

Upstream product

• 67-56-1 methanol 
• 114873-03-9 (2S)-2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)propanoic acid 
• 625-99-0 3-iodochlorobenzene 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 74-88-4 methyl iodide 

Downstream Products

• 942070-92-0 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate 
• 1364705-24-7 (S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid 
• 1364706-18-2 Ac-(cyclo-m,m)-[(3-Cl)FAAAY]-CO₂Me 
• 1364705-79-2 Boc-(cyclo-m,m)-[(3-Cl)FAAY]-CO₂Me 
• 1364705-55-4 Ac-(cyclo-m,m)-[(3-Cl)FAY]-CO₂Me 
• 1364705-47-4 Boc-(cyclo-m,m)-[(3-Cl)FAY]-CO₂Me 

Relevant academic research and scientific papers

Evidence for the role of tetramethylethylenediamine in aqueous negishi cross-coupling: Synthesis of nonproteinogenic phenylalanine derivatives on water

The structure of the alkylzinc-tetramethylethylenediamine (TMEDA) cluster cation 3 has been determined in the gas phase by a combination of tandem mass spectrometry, infrared multiphoton dissociation (IRMPD) spectroscopy, and DFT calculations. Both sets of experimental results establish the existence of a strongly stabilizing interaction of TMEDA with the zinc cation. High-level DFT calculations on the alkylzinc-TMEDA cluster cation 3 allowed the identification of two low energy conformers, each featuring a four-coordinate zinc atom with a bidentate TMEDA ligand, and internal coordination from the carbonyl group of the Boc group to zinc. The experimental IRMPD spectrum is reproduced with an appropriately weighted combination of the IR spectra of the two conformers identified by theory. DFT calculations on the structure of the alkylzinc halide 2 with coordinated TMEDA using the PCM model of water solvent suggest that TMEDA can promote ionization of the zinc-iodine bond in organozinc iodides under aqueous conditions, providing a credible explanation for the role of TMEDA in stabilizing the carbon-zinc bond. Reaction of the serine-derived iodide 1 with aryl iodides "on water", promoted by nano zinc in the presence of PdCl2 (Amphos) 2 (5 mol %) and TMEDA, leads to the formation of protected phenylalanine derivatives 4 in reasonable yields. In the case of ortho-substituted aryl iodides and aryl iodides that are solids at room temperature, conducting the reaction at 65°C gives improved results. In all cases, the product 5 of reductive dimerization of the iodide 1 is also isolated.

Functionalization of aromatic amino acids via direct C-H activation: Generation of versatile building blocks for accessing novel peptide space

Functionalized α-amino acid building blocks have been prepared in good yield with high regiocontrol and preservation of stereochemistry via iridium-catalyzed borylation of suitably protected aromatic α-amino acid derivatives. The utility of these systems

GLYT2 MODULATORS

α-, β-, and γ-amino acid derivatives of formula I are disclosed as selective GlyT2 inhibitors for the treatment of central nervous system (CNS) conditions such as muscle spasticity, tinnitus, epilepsy and neuropathic pain. Formula I