59490-36-7

Upstream product

• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 100-07-2 4-methoxy-benzoyl chloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 100-09-4 4-methoxybenzoic acid 
• 200353-70-4 1H-benzo[d][1,2,3]triazol-1-yl 4-methoxybenzoate 
• 103678-74-6 N-(4-methoxybenzoyl)-phenylalanine 
• 67-56-1 methanol 
• 217446-35-0 4-benzyl-2-(4-methoxyphenyl)-5-oxo-4,5-dihydrooxazole 
• 59490-27-6 methyl (Z)-2-(4-methoxybenzamido)-3-phenylacrylate 
• 34108-13-9 2-(p-Methoxyphenyl)-4-benzylidene-2-oxazolin-5-one 

Downstream Products

• 91373-74-9 (2S)-2--3-phenyl-1-propanol 
• 103678-74-6 (4-methoxybenzoyl)-L-phenylalanine 
• 1370731-51-3 methyl 2-(p-methoxylphenyl)-5-phenyloxazole-4-carboxylate 
• 1158827-37-2 C₁₇H₁₉N₃O₃ 
• 132207-11-5 (2S)-1-azido-2--3-phenyl-propane 
• 132233-11-5 (4S)-4-benzyl-3-(p-methoxybenzyl)-1,2,3-oxothiazolidine S,S-dioxide 
• 132207-12-6 (3S)-3--4-phenylbutyronitrile 
• 132207-13-7 (4S)-4-benzyl-3-(p-methoxybenzyl)-1,2,3-oxothiazolidine S-oxide 
• 132207-10-4 (2S)-1-fluoro-2--3-phenyl-propane 
• 169905-22-0 N-(tert-Butoxycarbonyl)-N-(4-methoxybenzyl)-L-phenylalaninol 
• 852468-46-3 ethyl (2R)-2-[(3S,4S)-3-benzyl-2-(4-methoxybenzyl)-1-oxo-2-azaspiro[4.5]decan-4-yl]propanoate 
• 852468-42-9 ethyl (4S,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate 
• 852468-43-0 ethyl (4S,2Z)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate 
• 852468-44-1 ethyl (4S,2E)-4-(4-methoxybenzylamino)-2-methyl-5-phenylpent-2-enoate 

Relevant academic research and scientific papers

Crystal structure of 1-(2,4,6-trichlorobenzoyloxy) benzotriazole (TCB-OBt): observation of uncommon intermolecular oxygen-oxygen interaction and synthetic application in amidation

Herein, we investigated the supramolecular assembly of a modified Yamaguchi reagent TCB-OBt. Interestingly, each molecule is interconnected through novel chalcogen-chalcogen (O?O) interaction, π-π stacking, and aromatic C-H?O interaction. Hirshfeld surface analysis confirmed the existence of uncommon O?O interactions. A well-organized supramolecular layer structure and helical arrangement were observed in the crystal structure. TCB-OBt crystallized in the O-substituted desmotropic form. DFT calculations suggest that the O-substituted form is more stable than theN-substituted form (TCB-(N)-OBt). Morphology analysis indicates the formation of a fantastically well organized, continuous block-shaped system. Furthermore, the designed reagent works as an efficient activating reagent for amide bond formation with good yields under mild reaction conditions. Use of this reagent avoided intractable acid chlorides, and this new mixed-anhydride-based reagent may further be applicable for many other organic transformations.

Rational Design of 2-Substituted DMAP- N-oxides as Acyl Transfer Catalysts: Dynamic Kinetic Resolution of Azlactones

A novel concept that conversion of chiral 2-substituted DMAP into its DMAP-N-oxide could significantly enhance the catalytic activity and still be used as an acyl transfer catalyst is presented. A new type of chiral 2-substituted DMAP-N-oxides, derived from l-prolinamides, has been rationally designed, facilely synthesized, and applied in the dynamic kinetic resolution of azlactones. Using simple MeOH as the nucleophile, various l-amino acid derivatives were produced in high yields (up to 98% yield) and enantioselectivities (up to 96% ee). Furthermore, α-deuterium labeled l-phenylalanine derivative was also obtained. Experiments and DFT calculations revealed that in 2-substituted DMAP-N-oxide, the oxygen atom acted as the nucleophilic site and the N-H bond functioned as the H-bond donor. High enantioselectivity of the reaction was governed by steric factors, and the addition of benzoic acid reduced the activation energy by participating in the construction of a H-bond bridge. The theoretical chemical study indicated that only when attack directions of the chiral catalyst were fully considered could the correct calculation results be obtained. This work paves the way for the utilization of the C2 position of the pyridine ring and the development of chiral 2-substituted DMAP-N-oxides as efficient acyl transfer catalysts.

Nickel-Catalyzed Asymmetric Hydrogenation of 2-Amidoacrylates

Earth-abundant nickel, coordinated with a suitable chiral bisphosphine ligand, was found to be an efficient catalyst for the asymmetric hydrogenation of 2-amidoacrylates, affording the chiral α-amino acid esters in quantitative yields and excellent enantioselectivity (up to 96 % ee). The active catalyst component was studied by NMR and HRMS, which helped us to realize high catalytic efficiency on a gram scale with a low catalyst loading (S/C=2000). The hydrogenated products could be simply converted into chiral α-amino acids, β-amino alcohols, and their bioactive derivatives. Furthermore, the catalytic mechanism was investigated using deuterium-labeling experiments and computational calculations.

Discovery of Novel Peptidomimetic Boronate ClpP Inhibitors with Noncanonical Enzyme Mechanism as Potent Virulence Blockers in Vitro and in Vivo

Caseinolytic protease P (ClpP) is considered as a promising target for the treatment of Staphylococcus aureus infections. In an unbiased screen of 2632 molecules, a peptidomimetic boronate, MLN9708, was found to be a potent suppressor of SaClpP function. A time-saving and cost-efficient strategy integrating in silico position scanning, multistep miniaturized synthesis, and bioactivity testing was deployed for optimization of this hit compound and led to fast exploration of structure-activity relationships. Five of 150 compounds from the miniaturized synthesis exhibited improved inhibitory activity. Compound 43Hf was the most active inhibitor and showed reversible covalent binding to SaClpP while did not destabilize the tetradecameric structure of SaClpP. The crystal structure of 43Hf-SaClpP complex provided mechanistic insight into the covalent binding mode of peptidomimetic boronate and SaClpP. Furthermore, 43Hf could bind endogenous ClpP in S. aureus cells and exhibited significant efficacy in attenuating S. aureus virulence in vitro and in vivo.

Intramolecular Diels-Alder Cycloaddition Approach toward the cis-Fused Δ5,6-Hexahydroisoindol-1-one Core of Cytochalasins

Synthesis of the cis-fused Δ5,6-hexahydroisoindol-1-one core of cytochalasins B2-B5, K, Z8, Z9, Z12-Z15, and Z17 has been established starting from an intramolecular D

Synthesis and antiviral activities of novel acylhydrazone derivatives targeting HIV-1 capsid protein

HIV-1 capsid protein (CA) plays important roles in the viral replication cycle. A number of acylhydrazone derivatives that act as inhibitors of HIV-1 CA assembly, were designed and synthesized. The synthesized compounds were tested for their antiviral activities and cytotoxicities using CEM cells. Some derivatives also were assayed for their ability to inhibit HIV-1 CA assembly in vitro. Among them, compounds 14f and 14i display the most promising potency with EC50 values of 0.21 and 0.17 μΜ, respectively.

Design, synthesis and SAR studies of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine as aminopeptidase N/CD13 inhibitors

Aminopeptidase N (APN), belonged to metalloproteinase, is an essential peptidase involved in the process of tumor invasion and metastasis. A series of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine were designed, synthesized and evaluate

Dynamic kinetic resolution during iron carbonyl promoted [6+2] ene-type reactions

Intramolecular coupling of cyclohexadiene-Fe(CO)3 complexes with pendant alkenes, to form spirolactams, proceed with excellent stereocontrol, using chiral amide substrates that lead to dynamic kinetic resolution.