888298-05-3

Usage

Uses

Used in Pharmaceutical Industry:
[(1R)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester is used as a precursor in the synthesis of various drugs for different health conditions. Its chemical structure allows for the development of medications with diverse pharmacological properties, making it a valuable asset in drug discovery and development.
Used in Drug Synthesis:
[(1R)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester is used as a versatile intermediate in the synthesis of pharmaceuticals. Its benzyl group attachment to the carbamic acid derivative provides a foundation for the creation of a wide range of drug molecules, enhancing the therapeutic options available for various health conditions.
Used in Medication Production:
[(1R)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester is used in the production of medications for various health conditions. Its potential applications in the pharmaceutical industry make it a promising candidate for the development of new treatments and therapies, contributing to advancements in healthcare and medicine.

Upstream product

• 14593-04-5 3-amino-3-phenyl-1-propanol 
• 501-53-1 benzyl chloroformate 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 678991-36-1 E-(+)-(1'S,2'S)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-3-phenylprop-2-enamide 
• 1202160-37-9 3-Cbz-4-phenyl-[1,2,3]oxathiazinane 2,2-dioxide 
• 77118-87-7 (S)-1-Phenyl-3-buten-1-ol 
• 100-52-7 benzaldehyde 
• 37088-68-9 methyl (S)-3-amino-3-phenylpropanoate tartaric salt 
• 14441-08-8 (3S)-N-(benzyloxycarbonyl)-3-amino-3-phenylpropanoic acid 
• 32975-59-0 methyl (S)-β-[[(phenylmethoxy)carbonyl]amino]-benzenepropanoate 
• 14898-52-3 methyl 3-amino-3-phenylpropanoate 
• 678991-41-8 (+)-(1'S,2'S,3S)-3-dibenzylamino-N-methyl-3-phenyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)propanamide 
• 102-92-1 Cinnamoyl chloride 
• 31139-36-3 dibenzyl dicarbonate 

Relevant academic research and scientific papers

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.

Syntheses of a flobufen metabolite and dapoxetine based on enantioselective allylation of aromatic aldehydes

The enantioselective allylation of an aromatic aldehyde to give a chiral homoallylic alcohol was employed as the key step in the syntheses of a flobufen metabolite and dapoxetine. In the former case, the homoallylic alcohol moiety (99 % ee) was converted into a five-membered lactone ring with good preservation of the optical purity, and the target compound, a flobufen metabolite, was obtained in 95 % ee. In the latter case, the homoallylic alcohol moiety (97 % ee) was transformed over several steps into a 3-aminopropanol moiety. During the course of the synthesis, the gradual loss of optical purity was observed, and the target compound, dapoxetine, was obtained in 85 % ee. The enantioselective allylation of an aromatic aldehyde to give the corresponding homoallylic alcohol was the key step in the syntheses of a flobufen metabolite and dapoxetine. In the first case, the homoallylic moiety was converted into a chiral five-membered lactone ring. In the second case, it was transformed into a chiral 1,3-amino alcohol moiety. Copyright

FUSED TRIAZOLE AMINES AS P2X7 MODULATORS

Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein X, Y, R1, R2, and R3 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of dise

Asymmetric synthesis of maraviroc (UK-427,857)

The asymmetric synthesis of Maraviroc (UK-427,857), a chemochine receptor 5 (CCR-5) receptor antagonist, based on an expeditious organocatalytic enantioselective assembly of the chiral βamino aldehyde key fragment is presented. The reactions were performed on a gram-scale and allow for the rapid construction of new Maraviroc analogues.

Highly efficient, enantioselective syntheses of (S)-(+)- and (R)-(-)-dapoxetine starting with 3-phenyl-1-propanol

(Chemical Equation Presented) A highly efficient, enantioselective sequence has been developed for the synthesis of (S)- and (R)-dapoxetine. The pathways involve the intermediacy of the 6-membered-ring sulfamate esters 4, which were generated by Du Bois asymmetric C-Hamination reactions of the prochiral sulfamate 3, catalyzed by the chiral dirhodium(II) complexes. During the course of our research, the absolute configuration of the enantiomer of 4-pheny[1,2,3]oxathiazinane 2,2-dioxide (4r), prepared by the Du Bois asymmetric C-H amination reaction of 3 and the Rh2(S-nap)4 catalyst, is determined to be R and not S as was originally reported.

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.

A general and enantiodivergent method for the asymmetric synthesis of piperidine alkaloids: concise synthesis of (R)-pipecoline, (S)-coniine and other 2-alkylpiperidines

A simple and very efficient protocol for the preparation of highly enantioenriched 2-alkylpiperidines has been set up, which allows the preparation of the final heterocycles with any wanted configuration at the stereogenic center starting from the same starting material. The key step of the synthesis relies on a diastereodivergent aza-Michael reaction protocol using the readily available and cheap reagent (+)-(S,S)-pseudoephedrine as chiral auxiliary.

Lipase-catalyzed resolution of chiral 1,3-amino alcohols: application in the asymmetric synthesis of (S)-dapoxetine

The enzymatic resolution of 3-amino-3-phenylpropan-1-ol derivatives has been studied through acylation processes. Candida antarctica lipase A (CAL-A) has been identified as the best biocatalyst for the transesterification reaction of 3-amino-3-phenyl-1-tert-butyldimethylsilyloxy-propan-1-ol using ethyl methoxyacetate as acylating agent and tert-butyl methyl ether as solvent. This enzymatic study has allowed us to obtain a valuable intermediate for the production of (S)-dapoxetine, which has been synthesized in good overall yield and high enantiomeric excess.

(S,S)-(+)-pseudoephedrine as chiral auxiliary in asymmetric aza-Michael reactions. Unexpected selectivity change when manipulating the structure of the auxiliary

The asymmetric aza-Michael reaction of metal benzylamides to α,β-unsaturated amides derived from the chiral amino alcohol (S,S)-(+)-pseudoephedrine has been studied in detail. A deep study of the most important experimental parameters (solvent, temperatur