Awesome and Easy Science Experiments about (R)-4-Benzyl-2-oxazolidinone

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PYRIDIN-2-YL ALKYLAMINO SUBSTITUTED HYDROXAMIC ACID AND USES THEREOF

Compounds of formula I are provided: wherein X is NH, or CH2, Y is a single bond, or -CHR5-, R1 is H, C1-C4 alkyl, or C1-C4 hydroxyalkyl, R2 and R2′ are each independently H, C1-C4 alkyl, or C1-C4 hydroxyalkyl, each R3 is independently H, halo, -CF3, C1-C4 alkyl, or C1-C4 alkoxy, C3 perhaloalkyl, each R4 is independently H, halo, or C1-C4 alkyl, R5 is C1-C4 alkoxy, r is integer from 0 to 3; and p is integer from 0 to 3.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H1615NO – PubChem

 

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New Routes to Chiral Evans Auxiliaries by Enzymatic Desymmetrisation and Resolution Strategies

This paper describes how enantiomerically enriched Evans auxiliaries can be successfully prepared by either an enzymatic desymmetrisation strategy or an asymmetric synthesis using racemic auxiliaries and an enzymatic resolution. Desymmetrisation of N-Boc-protected serinol has been achieved in good yield and high enantiomeric excess using porcine pancreas lipase. This has been exploited in different ways to prepare enantiomerically enriched (4R)- and (4S)-substituted 2-oxazolidinones. In another approach to asymmetric synthesis, starting from a racemic Evans auxiliary, by means of a diastereoselective aldol reaction coupled with a lipase-catalysed resolution, we achieved the preparation of enantiomerically enriched beta-hydroxy acids and enantiomerically enriched 2-oxazolidinones.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1945NO – PubChem

 

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Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy

A direct and general method for the synthesis of naturally occurring 2,3,4,5,6-pentasubstituted tetrahydropyrans has been developed, employing beta,gamma-unsaturated N-acyl oxazolidin-2-ones as key starting materials. The combination of the Evans aldol addition and the Prins cyclization allowed the diastereoselective and efficient generation of the desired oxacycles in two fashions: a one-pot Evans aldol-Prins protocol, in which five new sigma bonds and five contiguous stereocenters were straightforwardly generated, and a two-step version, which additionally permitted the isolation of beta,gamma-unsaturated alcohol precursors bearing an N-acyl oxazolidin-2-one in the alpha position. From these alcohols were also obtained halogenated pentasubstituted tetrahydropyrans as well as 2,3,4,5-tetrasubstituted tetrahydrofurans, shedding light on the mechanism of the process. Computational studies were consistent with the experimental findings, and this innovative Evans aldol-Prins strategy was performed for the preparation of a battery of more than 30 densely substituted tetrahydropyrans, unprecedentedly fused to a 1,3-oxazinane-2,4-dione ring, both in a racemic fashion and in an enantiomeric fashion. These novel molecules were successfully submitted to several transformations to permit simple access to a variety of differently functionalized tetrahydropyrans. Most of these unique molecules were evaluated for their antimicrobial activity against Gram-positive and Gram-negative bacteria and the yeast Candida albicans, and some structure-activity relationships were established.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1714NO – PubChem

 

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Stereoselective Simmons-Smith cyclopropanation of chiral enamides

(Chemical Equation Presented) Efficient and practical access to chiral aminocyclopropanes is secured by the title reaction (see example). Both E and Z enamides undergo the cyclopropanation with high diastereoselectivity (d.r. up to > 95:5). The application of this methodology to the synthesis of biologically significant aminocyclopropanes illustrates the potential of chiral enamides as useful building blocks for stereoselective organic synthesis.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2026NO – PubChem

 

The important role of (R)-4-Benzyl-2-oxazolidinone

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Enantioselective Total Synthesis of Antibiotic CJ-16,264, Synthesis and Biological Evaluation of Designed Analogues, and Discovery of Highly Potent and Simpler Antibacterial Agents

An improved and enantioselective total synthesis of antibiotic CJ-16,264 through a practical kinetic resolution and an iodolactonization reaction to form the iodo pyrrolizidinone fragment of the molecule is described. A series of racemic and enantiopure analogues of CJ-16,264 was designed and synthesized through the developed synthetic technologies and tested against drug-resistant bacterial strains. These studies led to interesting structure-activity relationships and the identification of a number of simpler, and yet equipotent, or even more potent, antibacterial agents than the natural product, thereby setting the foundation for further investigations in the quest for new anti-infective drugs.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1951NO – PubChem

 

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A palladium-catalyzed domino reaction as key step for the synthesis of functionalized aromatic amino acids

A variety of substituted aromatic systems are synthesized by the Catellani reaction. These are used as precursors for novel amino acids with a basic side chain. Georg Thieme Verlag Stuttgart New York.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2029NO – PubChem

 

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Concise asymmetric routes to 2,2,4-trisubstituted tetrahydrofurans via chiral titanium imide enolates: Key intermediates towards synthesis of highly active azole antifungals Sch 51048 and Sch 56592

Two complimentary approaches to the key (-)-(2R)-cis-tosylate 1 and its (+)-(2S)-enantiomer 15 via generation of chiral imide enolates having a 2,2-disubstituted olefin functionality in the beta-position, are described. In a ‘protecting group free’ sequence, reaction of the titanium enolate generated from (4R)-benzyl-2-oxazolidinone derived imide 5b with s-trioxane provided a convenient intermediate 19 which could be directly subjected to 2,4-diastereoselective iodocyclization.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2005NO – PubChem

 

Simple exploration of (R)-4-Benzyl-2-oxazolidinone

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CARBAZOLE-CONTAINING AMIDES, CARBAMATES, AND UREAS AS CRYPTOCHROME MODULATORS

The subject matter herein is directed to carbazole-containing amide, carbamate, and urea derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R1, R2, R3, R4, R5, R6, R7, A, D, E, G, J, L, M, Q, a, and b are accordingly described. Also provided are pharmaceutical compositions containing the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, complications associated with diabetes, Cushing’s syndrome, NASH, NAFLD, asthma, and COPD.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1556NO – PubChem

 

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Efficient diastereoselective synthesis of (2R,3R,4R)-2-amino-3-hydroxy-4,5- dimethylhexanoic acid, the lactone linkage unit of homophymine A

For the total synthesis of novel cyclodepsipeptide homophymine A, (2R,3R,4R)-2-amino-3-hydroxy-4,5- dimethylhexanoic acid was successfully synthesized by Evans’ asymmetric alkylation and the anti-selective asymmetric hydrogenation of a chiral alpha-amino-beta-keto ester as the key steps.

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Oxazolidine – Wikipedia,
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Racemic auxiliaries: Applications to asymmetric synthesis

Racemic auxiliaries have been successfully used to achieve asymmetric synthesis. Racemic Evans aldol products were obtained from racemic acyl oxazolidinones with good diastereocontrol. The enantiomers of the racemic aldol products were resolved by a lipase-catalysed acylation reaction. Hydrolysis afforded enantiomerically enriched oxazolidinones and enantiomerically enriched beta-hydroxy acids.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1946NO – PubChem