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Usage

Uses

Used in Organic Synthesis:
(S)-4-(1-Isopropyl)-3-(1-oxobutyl)-2-oxazolidinone is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure and chiral center make it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-4-(1-Isopropyl)-3-(1-oxobutyl)-2-oxazolidinone is used as a key component in the development of chiral drugs. Its specific stereochemistry allows for the creation of enantiomerically pure compounds, which is essential for ensuring the desired biological activity and minimizing potential side effects.
Used in Chiral Pool Synthesis:
(S)-4-(1-Isopropyl)-3-(1-oxobutyl)-2-oxazolidinone is utilized as a chiral pool compound in the synthesis of enantiomerically pure molecules. Its presence in the reaction mixture can help to induce chirality in the final product, facilitating the production of single enantiomers with desired properties.
Used in Asymmetric Catalysis:
(S)-4-(1-Isopropyl)-3-(1-oxobutyl)-2-oxazolidinone is also employed in asymmetric catalysis, where it can serve as a ligand or a catalyst precursor. Its chiral structure can help to control the stereochemistry of the reaction, leading to the formation of enantiomerically enriched products.

Upstream product

• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 
• 141-75-3 butyryl chloride 
• 2026-48-4 (S)-valinol 

Downstream Products

• 103422-97-5 (4S,2'S)-3-<2-(((benzyloxy)carbonyl)oxy)-1-oxobutyl>-4-isopropyloxazolidin-2-one 
• 142542-55-0 3-<1-oxo-2(S)-<<(phenylmethyl)thio>methyl>butyl>-4(S)-(1-methylethyl)-2-oxazolidinone 

Relevant academic research and scientific papers

Syntheses of isotopically labelled L-?±-amino acids with an asymmetric centre at C-3

Approaches are described to the synthesis of a series of isotopically labelled L-a-amino acids each with an asymmetric centre at C-3, including isoleucine, allo-isoleucine, threonine and allo-threonine. The methods may be simply adapted for the selective incorporation of an isotopic label at each site of L-valine including the selective labelling of either diastereotopic methyl group with carbon-13 and/or deuterium and labelling of the amine with nitrogen-15. ? The Royal Society of Chemistry 2000.

Unsaturated hydroxyalkylquinoline acids as leukotriene antagonists

Compounds having the formula I: STR1 are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection.

Chemo-enzymatic synthesis of isotopically labelled L-valine, L-isoleucine and allo-isoleucine

Syntheses of (3R)-[4,4,4-D3]-L-valine, [15N]-L-isoleucine and [15N]-allo-isoleucine from homochiral 2-alkylated carboxylic acids are described. The approach involves a one-carbon homologation of the carboxylic acid to give

Thiopyrano[2,3,4-cd]indoles as 5-lipoxygenase inhibitors: Synthesis, biological profile, and resolution of 2-[2-[1-(4-chlorobenzyl)-4-methyl-6- [(5-phenylpyridin-2-yl)methoxy]-4,5-dihydro-1H-thiopyrano[2,3,4-cd]indol-2- yl]ethoxy]butanoic acid

Leukotriene biosynthesis inhibitors have potential as new therapies for asthma and inflammatory diseases. The recently disclosed thiopyrano[2,3,4- cd]indole class of 5-lipoxygenase (5-LO) inhibitors has been investigated with particular emphasis on the side chain bearing the acidic functionality. The SAR studies have shown that the inclusion of a heteroatom (O or S) in conjunction with an α-ethyl substituted acid leads to inhibitors of improved potency. The most potent inhibitor prepared contains a 2-ethoxybutanoic acid side chain. This compound, 14d (2-[2-[1-(4-chlorobenzyl)-4-methyl-6-[(5- phenylpyridin-2-yl)methoxy]-4,5-dihydro-1H-thiopyrano[2,3,4-cd]indol-2- yl]ethoxy]butanoic acid, L-699,333), inhibits 5-HPETE production by human 5- LO and LTB4 biosynthesis by human PMN leukocytes and human whole blood (IC50s of 22 nM, 7 nM and 3.8 μM, respectively). The racemic acid 14d has been shown to be functionally active in a rat pleurisy model (inhibition of LTB4, ED50 = 0.65 mg/kg, 6 h pretreatment) and in the hyperreactive rat model of antigen-induced dyspnea (50% inhibition at 2 and 4 h pretreatment; 0.5 mg/kg po). In addition, 14d shows excellent functional activity against antigen-induced bronchoconstriction in the conscious squirrel monkey [89% inhibition of the increase in R(L) and 68% inhibition in the decrease in C(dyn) (0.1 mg/kg, n = 3)] and in the conscious sheep models of asthma (iv infusion at 2.5 μg/kg/min). Acid 14d is highly selective as an inhibitor of 5-LO activity when compared to the inhibition of human 15-LO, porcine 12-LO and ram seminal vesicle cyclooxygenase (IC50 > 5 μM) or competition in a FLAP binding assay (IC50 > 10 μM). Resolution of 14d affords 14g, the most potent diastereomer, which inhibits the 5-HPETE production of human 5-LO and LTB4 biosynthesis of human PMN leukocytes and human whole blood with IC50s of 8 nM, 4 nM, and 1 μM respectively. The in vitro and in vivo profile of 14d is comparable to that of MK-0591, which has showed biochemical efficacy in inhibiting ex vivo LTB4 biosynthesis and urinary LTE4 excretion in clinical trials.

Fluorinated hydroxyalkylquinoline acids as leukotriene antagonists

Compounds having the formula I: STR1 are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection.