32975-59-0

Usage

Uses

Used in Pharmaceutical Industry:
N-Benzyl (S)-β-(CarboxyaMino)-hydrocinnaMic Acid Methyl Ester is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications, such as antibiotics, anti-inflammatory agents, and analgesics.
Used in Organic Synthesis:
In the field of organic synthesis, N-Benzyl (S)-β-(CarboxyaMino)-hydrocinnaMic Acid Methyl Ester serves as a versatile building block for the creation of complex organic molecules. Its reactivity and functional groups enable chemists to perform a wide range of reactions, such as amide coupling, esterification, and transesterification, to construct diverse molecular architectures.
Used in Research and Development:
N-Benzyl (S)-β-(CarboxyaMino)-hydrocinnaMic Acid Methyl Ester is also utilized in research and development settings, where it can be employed to study the properties and reactivity of similar molecules. Researchers can use N-Benzyl (S)-β-(CarboxyaMino)-hydrocinnaMic Acid Methyl Ester to investigate new synthetic routes, reaction mechanisms, and the development of novel catalysts or reagents.
Used in Material Science:
N-Benzyl (S)-β-(CarboxyaMino)-hydrocinnaMic Acid Methyl Ester can be incorporated into the design and synthesis of new materials, such as polymers, coatings, and adhesives. Its functional groups and molecular structure can contribute to the development of materials with improved properties, such as enhanced stability, adhesion, or biocompatibility.

Upstream product

• 67-56-1 methanol 
• 32975-58-9 (R)-(-)-α-benzyloxycarbonylaminobenzyldiazomethyl ketone 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 37088-66-7 (3S)-methyl 3-amino-3-phenylpropanoate 
• 501-53-1 benzyl chloroformate 
• 103-26-4 methyl cinnamate 
• 14898-52-3 methyl 3-amino-3-phenylpropanoate 
• 37088-68-9 methyl (S)-3-amino-3-phenylpropanoate tartaric salt 
• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 
• 159173-92-9 methyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-phenylpropanoate 
• 103-26-4 Methyl cinnamate 
• 64420-86-6 O-p-toluenesulfonyl benzyloxyhydroxamate 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 83649-47-2 (S)-(-)-β-Phenyl-β-alanine hydrochloride 
• 1419075-37-8 (S)-benzyl [5-(1,3-dioxoisoindolin-2-yl)-3-oxo-1-phenylpentyl]carbamate 
• 1419075-39-0 (S)-benzyl [2-(2-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-1,3-dioxan-2-yl)-1-phenylethyl]carbamate 
• 1419075-40-3 (S)-benzyl [2-(2-(2-aminoethyl)-1,3-dioxan-2-yl)-1-phenylethyl]carbamate 
• 1419075-42-5 (S)-benzyl [1-phenyl-2-(2-(2-(2,2,2-trifluoroacetamido)ethyl)-1,3-dioxan-2-yl)ethyl]carbamate 
• 1419075-43-6 (S)-N-(2-(2-(2-amino-2-phenylethyl)-1,3-dioxan-2-yl)ethyl)-2,2,2-trifluoroacetamide 
• 1419075-24-3 2,2,2-trifluoro-N-[(4E)-3-oxo-5-phenylpent-4-en-1-yl]acetamide 
• 14441-08-8 (3S)-N-(benzyloxycarbonyl)-3-amino-3-phenylpropanoic acid 
• 1419075-36-7 (S)-benzyl [1-phenyl-3-(4-morpholinyl)-3-oxopropyl]carbamate 
• 947530-18-9 (S)-benzyl [3-oxo-1-phenylpent-4-en-1-yl]carbamate 
• 947530-23-6 (S,E)-benzyl [3-oxo-1-phenyl-hex-4-enyl]carbamate 
• 947530-24-7 C₂₀H₂₁NO₃ 
• 874141-25-0 (-)-(3S)-3-(N-benzyloxycarbonylamino)-3-phenyl-(N'-methoxy-N'-methylpropananamide) 
• 1425666-99-4 (S)-benzyl [4-(diethoxyphosphoryl)-3-oxo-1-phenylbutyl]carbamate 

Relevant academic research and scientific papers

Multicomponent Catalytic Enantioselective Synthesis of Isoxazolidin-5-Ones

We report herein a strategy to afford a multicomponent catalytic enantioselective synthesis of β-substituted isoxazolidin-5-ones via a KMC process promoted by a suited cupreine used as bifunctional organocatalyst. The hydroxamic acid component, with a ste

Structure-Based Design and Development of Chemical Probes Targeting Putative MOR-CCR5 Heterodimers to Inhibit Opioid Exacerbated HIV-1 Infectivity

Crystal structures of ligand-bound G-protein-coupled receptors provide tangible templates for rationally designing molecular probes. Herein, we report the structure-based design, chemical synthesis, and biological investigations of bivalent ligands targeting putative mu opioid receptor C-C motif chemokine ligand 5 (MOR-CCR5) heterodimers. The bivalent ligand VZMC013 possessed nanomolar level binding affinities for both the MOR and CCR5, inhibited CCL5-stimulated calcium mobilization, and remarkably improved anti-HIV-1BaL activity over previously reported bivalent ligands. VZMC013 inhibited viral infection in TZM-bl cells coexpressing CCR5 and MOR to a greater degree than cells expressing CCR5 alone. Furthermore, VZMC013 blocked human immunodeficiency virus (HIV)-1 entry in peripheral blood mononuclear cells (PBMC) cells in a concentration-dependent manner and inhibited opioid-accelerated HIV-1 entry more effectively in phytohemagglutinin-stimulated PBMC cells than in the absence of opioids. A three-dimensional molecular model of VZMC013 binding to the MOR-CCR5 heterodimer complex is constructed to elucidate its mechanism of action. VZMC013 is a potent chemical probe targeting MOR-CCR5 heterodimers and may serve as a pharmacological agent to inhibit opioid-exacerbated HIV-1 entry.

Access to 2,6-disubstituted piperidines: Control of the diastereoselectivity, scope, and limitations. applications to the stereoselective synthesis of (-)-solenopsine A and alkaloid (+)-241D

Scope and limitations in the diastereoselective preparation of 2,6-cis or 2,6-trans disubstituted piperidines are described, through intramolecular reaction of chiral β′-carbamate-α,β-unsaturated ketone. This methodology has been applied to the total synthesis of a few well chosen examples, such as (-)-solenopsine A and alkaloid (+)-241D.

Efficient synthesis of β'-amino-α, β-unsaturated ketones

A general and simple procedure to access chiral β'-amino-α, β-enones, in seven steps, from an α,β unsaturated ester has been described. The use of a Horner-Wadsworth-Emmons reaction as a key step for generating the β'-amino-α,β-enones, permits access to a range of substrates under mild conditions and in moderate to high yield.

Stereoselective synthesis and in vivo evaluation of the analgesic activity of polysubstituted bispidines

Hetero-Michael addition on a chiral β'-amino α,β- unsaturated ketone gave, after some structural modifications, β,β'-diamino ketals. Mannich-type reactions of these diamines with an aldehyde led, with high diastereoselectivity, to trisubstituted piperidines. Another highly stereoselective Mannich cyclization, with an N-acyliminium ion generated in situ from the corresponding imide, allowed the preparation of original polycyclic bispidine derivatives. The antinociceptive effect of the three compounds prepared was evaluated in vivo by using the writhing test. If the biological results for the analgesic properties were disappointing, compared with the bispidine HZ2, which has a high affinity for opioid receptors, the modularity of the approach offered the possibility of introducing many substituents for new applications, which was promising because the bispidine core has been described to have many different activities. Total stereoselective synthesis of bispidine derivatives is achieved by using as two successive Mannich reactions key steps. This process constitutes a powerful approach toward the preparation of a polycyclic bispidine backbone with high enantioselectivity.

Catalytic asymmetric aziridination of α,β-unsaturated aldehydes

The development, scope, and application of the highly enantioselective organocatalytic aziridination of α,β-unsaturated aldehydes is presented. The aminocatalytic azirdination of α,β-unsaturated aldehydes enables the asymmetric formation of β-formyl aziri

Stereoselective chemoenzymatic preparation of β-amino esters: Molecular modelling considerations in lipase-mediated processes and application to the synthesis of (S)-dapoxetine

A wide range of optically active 3-amino-3-arylpropanoic acid derivatives have been prepared by means of a stereoselective chemoenzymatic route. The key step is the kinetic resolution of the corresponding β-amino esters. Although the enzymatic acylations of the amino group with ethyl methoxyacetate showed synthetically useful enantioselectivities, the hydrolyses of the ester group catalyzed by lipase from Pseudomonas cepacia have been identified as the optimal processes concerning both activity and enantioselectivity. The enantiopreference of this lipase in these reactions has been explained, at the molecular level, by using a fragment-based approach in which the most favoured binding site for a phenyl ring and the most stable conformation of the 3-aminopropanoate core nicely match the (S)-configuration of the major products. The conversion and enantioselectivity values of the enzymatic reactions have been compared in order to understand the influence of the different substitution patterns present in the phenyl ring. This chemoenzymatic route has been successfully applied to the preparation of a valuable intermediate in the synthesis of (S)-dapoxetine, which has been chemically synthesised in excellent optical purity.

Development of a bulk enabling route to maraviroc (UK-427,857), a CCR-5 receptor antagonist

A bulk enabling synthesis of the CCR-5 receptor antagonist, Maraviroc (UK-427,857) (1), is presented. Synthesis of the three key fragments, β-amino ester 3,4,4-difluorohexanecarboxylic acid (2), and 1,3,4-triazole-substituted tropane fragment 4 are described. Coupling strategies for these fragments are discussed and described, including synthetic challenges, protection strategies, impurity generation, and final scale-up of the developed route to 1.

Direct enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative

A highly enantioselective Mannich reaction between malonate esters and N-Boc and N-Cbz aldimines, catalysed by a bifunctional cinchonine derivative, has been developed; extension of this methodology to encompass the use of 2-substituted-1,3-dicarbonyl nuc

THIADIAZOLE AMIDE MMP INHIBITORS

The present invention provides novel thiadiazole amide derivatives represented by formula I The compounds of the present invention inhibit various enzymes from the matrix metalloproteinase family, predominantly stromelysins, and hence are useful f