131685-53-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-4-Benzyl-3-Propionyl-2-Oxazolidinone is used as a key intermediate in the synthesis of anisomycin analogues, which act as activators of the JNK/SAPK1 and p38/SAPK2 pathways. These pathways play a crucial role in cellular processes such as apoptosis, inflammation, and immune responses, making (R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE valuable in the development of pharmaceuticals targeting these pathways.
Used in Organic Synthesis:
(R)-(-)-4-Benzyl-3-Propionyl-2-Oxazolidinone is used as a building block for the preparation of complex organic molecules. One such application is in the synthesis of methyl 3-[(S)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methyl-3-oxopropyl]benzoate. This is achieved by treating the compound with a strong base, followed by the addition of methyl 3-bromomethyl benzoate, showcasing its utility in creating diverse chemical structures for various applications.

InChI:InChI=1/C13H15NO3/c1-2-12(15)14-11(9-17-13(14)16)8-10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3/t11-/m1/s1

Upstream product

• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 123-62-6 propionic acid anhydride 
• 79-03-8 propionyl chloride 
• 105-58-8 Diethyl carbonate 
• 90719-32-7 4-benzyl-2-oxazolidinone 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 802294-64-0 propionic acid 
• 111292-87-6 (R)-3-(1-butyryl)-4-benzyloxazolidine-2-one 
• 645386-89-6 (R)-4-benzyl-3-((S)-2-(benzyloxymethyl)butanoyl)-1,3-oxazolidin-2-one 
• 907593-86-6 (R)-4-benzyl-3-[(S)-2-(hydroxymethyl)butanoyl]oxazolidin-2-one 
• 1239664-46-0 (R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one 
• 352438-07-4 ⁽⁴⁵⁾-3-propionyl-4-benzyl-2-oxazolidinone 
• 1501971-59-0 (2R,3S,4R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2,4-dimethyl-1-oxohexan-3-yl-4-methylbenzenesulfonate 
• 1501971-58-9 (4R)-4-benzyl-3-((2R,3S,4R)-3-hydroxy-2,4-dimethylhexanoyl)oxazolidin-2-one 

Downstream Products

• 113453-28-4 <3(2S,3R,4E),4S>-3-(-3-hydroxy-2-methyl-1-oxo-5-phenyl-4-penteyl)-4-(phenylmethyl)-2-oxazolidinone 
• 141423-26-9 (S)-4-benzyl-3-((R,E)-2-methyl-5-phenylpent-4-enoyl)oxazolidin-2-one 
• 128329-56-6 (4S,2'R)-3-(3'-(benzyloxy)-2'-methylpropanoyl)-4-benzyl-1,3-oxazolidin-2-one 
• 139278-19-6 <3(2S,3R)4S>-3-<3-hydroxy-2-methyl-6-heptenoyl>-4-benzyl-2-oxazolidinone 
• 136546-79-7 <4S,3(2R)>-4-benzyl-3-<4-(tert-butoxycarbonyl)-2-methylbutanoyl>-2-oxazolidinone 
• 152899-15-5 <3(2'R),4S>-3-(2-Methyl-1-oxooctyl)-4-(phenylmethyl)-2-oxazolidinone 
• 138649-97-5 (4S)-3-<(2S,3S)-3-hydroxy-2-methyl-1-oxo-3-(1-phenylsulfanylcyclohexyl)propyl>-4-phenylmethyl-1,3-oxazolidin-2-one 
• 126788-79-2 (S)-4-Benzyl-3-[(E)-3-hydroxy-5-(3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-pent-4-enoyl]-oxazolidin-2-one 
• 124356-91-8 (4S,2'S,3'R)-3-(2'-methyl-3'-hydroxypentanoyl)-4-benzyl-2-oxazolidinone 
• 158220-66-7 (S)-4-Benzyl-3-((R)-2-methyl-hex-4-ynoyl)-oxazolidin-2-one 
• 136546-77-5 (4R)-5-[(4S)-4-benzyl-2-oxooxazolidin-3-yl]-4-methyl-5-oxopentanenitrile 
• 136546-77-5 (S)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-4-methyl-5-oxo-pentanenitrile 
• 136546-78-6 methyl (R)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-methyl-5-oxopentanoate 
• 136546-78-6 (S)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-4-methyl-5-oxo-pentanoic acid methyl ester 

Relevant academic research and scientific papers

Thermal proteome profiling efficiently identifies ribosome destabilizing oxazolidinones

Identifying the targets of bioactive small molecules is a challenging endeavor for which no general solution currently exists. Classical affinity purification experiments suffer from the need to functionalise a bioactive compound and link it to a solid support, which may interfere with target binding. A modern mass spectrometry-based proteomics technique that has partially circumvented this problem is thermal proteome profiling (TPP), which determines the effect of an unmodified small molecule on the thermal stability of the whole proteome simultaneously. Here, we use TPP to identify the mode-of-action of a newly-discovered autophagy inhibitor based on oxazolidinones often employed as chiral auxiliaries. Surprisingly, a significant portion of all ribosomal proteins were found to be destabilized by the inhibitor, highlighting the utility of this technology for determining a challenging mode-of-action.

SUBSTITUTED TETRAHYDROFURANS AS MODULATORS OF SODIUM CHANNELS

Compounds, and pharmaceutically acceptable salts thereof, useful as inhibitors of sodium channels are provided. Also provided are pharmaceutical compositions comprising the compounds or pharmaceutically acceptable salts and methods of using the compounds, pharmaceutically acceptable salts, and pharmaceutical compositions in the treatment of various disorders, including pain.

Synthesis and Bioactivity of a Macrocidin B Stereoisomer

A stereoisomer of macrocidin B, a presumed metabolite of the fungus Phoma macrostoma, was synthesized in 18 steps and 2.7% yield from protected l-tyrosine that was N-β-ketoacylated with a fully functionalized octanoyl Meldrum's acid. Dieckmann condensation gave a 3-acyltetramic acid, which was macrocyclized via Williamson etherification between the phenol and epi-bromohydrin termini. This macrocidin B stereoisomer showed a weaker herbicidal effect than macrocidin A and no similar inhibitory effect on biofilms of Staphylococcus aureus.

A Synthesis Strategy for the Production of a Macrolactone of Gulmirecin A via a Ni(0)-Mediated Reductive Cyclization Reaction

A synthesis strategy for the production of a key synthetic intermediate of gulmirecin A was described. The key reaction in the preparation of the 12-membered macrolactone is the Ni(0)-mediated reductive cyclization reaction of ynal using an N-heterocyclic carbene ligand and silane reductant. In addition, the α-selective glycosylation reaction of the macrolactone was performed to demonstrate the synthesis of gulmirecin and disciformycin precursors.

Ring-closing metathesis approaches towards the total synthesis of rhizoxins

Efforts are described towards the total synthesis of the bacterial macrolide rhizoxin F, which is a potent tubulin assembly and cancer cell growth inhibitor. A significant amount of work was expanded on the construction of the rhizoxin core macrocycle by ring-closing olefin metathesis (RCM) between C(9) and C(10), either directly or by using relay substrates, but in no case was ringclosure achieved. Macrocycle formation was possible by ring-closing alkyne metathesis (RCAM) at the C(9)/C(10) site. The requisite diyne was obtained from advanced intermediates that had been prepared as part of the synthesis of the RCM substrates. While the direct conversion of the triple bond formed in the ring-closing step into the C(9)-C(10) E double bond of the rhizoxin macrocycle proved to be elusive, the corresponding Z isomer was accessible with high selectivity by reductive decomplexation of the biscobalt hexacarbonyl complex of the triple bond with ethylpiperidinium hypophosphite. Radical-induced double bond isomerization, full elaboration of the C(15) side chain, and directed epoxidation of the C(11)-C(12) double bond completed the total synthesis of rhizoxin F.

Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety

Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.

Total synthesis of natural (?)- and unnatural (+)-Melearoride A

This communication details the first total synthesis of the 13-membered macrolide, (?)-Melearoride A, as well as unnatural (+)-Melearoride A. The synthesis features a concise 13 step synthesis (11 steps longest linear sequence) that offers flexible stereo-control and multiple opportunities for unnatural analog synthesis to delve into antifungal SAR. The route features a cuprate addition, an Evans asymmetric alkylation, and a ring-closing metathesis (RCM) to close the 13-membered macrocyclic core.

Bombyx uterol ester (((R)-(-)-3-2- R) and its derivatives) and synthetic method thereof (by machine translation)

The invention discloses a synthetic method of ((R)- (-) - 3 - rhodanshi ester (R)-2-methyl) propionate (methyl propionate) and a derivative thereof. To the synthetic method disclosed by the (S)- 4 - invention, as a raw material, a series of reactions such as acylation, substitution, hydrolysis, esterification, hydrogenation and ((R)- (-) - 3 - the like are synthesized to synthesize the Rogoligoligoligoligosl)-methyl propionate and derivatives thereof. The synthesis method is equally applicable to the synthesis of its enantiomers and derivatives thereof. The method has the advantages of short reaction time, high yield, good chiral selectivity, suitability for industrial production and the like. The invention relates to a roshi ester and a derivative structure thereof. . (by machine translation)

Controllable Intramolecular Unactivated C(sp3)-H Amination and Oxygenation of Carbamates

Dual catalyst-controlled intramolecular unactivated C(sp3)-H amination and oxygenation of carbamates merging visible-light photocatalysis and earth-abundant transition metal catalysis have been reported. Useful amino alcohol and diol derivatives could be selectively obtained from readily available tertiary alcohol derivatives. The possible mechanisms have been proposed via a 1,5-HAT process followed by Lewis acid-controlled cyclization. The nickel and zinc catalysts inhibit the formation of oxygenation and amination products, respectively. An interesting phenomenon of chirality transfer is also observed.

A method for synthesis of acylated oxazolidone

The invention discloses a method for synthesis of acylated oxazolidone. Synthesis method of the invention, comprising the following steps: in the non-protic organic solvent, the compound III and under the action of an acid, the compound I with compound II carries out amidation reaction, to obtain compound IV. The method of the invention can be conducted under mild conditions, high yield, high purity, and is suitable for industrial production requirements.