Month: October 2022

On March 28, 2013, Guo, Bin; Fan, Houxing; Xin, Qisheng; Chu, Wenjing; Wang, Hui; Huang, Yanqin; Chen, Xiaoyan; Yang, Yushe published an article.Application In Synthesis of (R)-5-(Hydroxymethyl)oxazolidin-2-one The title of the article was Solubility-Driven Optimization of (Pyridin-3-yl) Benzoxazinyl-oxazolidinones Leading to a Promising Antibacterial Agent. And the article contained the following:

The solubility-driven structural modification of substituted (pyridin-3-yl)-containing hydrobenzo[b]oxazolo[3,4-d][1,4]oxazinones is described, which resulted in the development of a new series of benzo[b]oxazolo[3,4-d][1,4]oxazinone analogs with high antibacterial activity against Gram-pos. pathogens, including that against linezolid-resistant strains, and low hERG inhibition. With regard to structure-activity relationship (SAR) trends among the various substituents on the pyridyl ring, relatively small and nonbasic substituents were preferable to sterically demanding or basic substituents. Oxazolidinone ring substitution on the pyridyl ring generated analogs with antibacterial activity superior to imidazolidinone ring. Solubility was enhanced by the incorporation of polar groups, especially when compounds were converted to their prodrugs. Among the prodrugs, compound I exhibited excellent solubility and a good pharmacokinetic profile. In a MRSA systemic infection model, compound I displayed an ED50 = 5.00 mg/kg, a potency that is 2-fold better than that of linezolid. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).Application In Synthesis of (R)-5-(Hydroxymethyl)oxazolidin-2-one

The Article related to oxazolooxazinone pyridyl substituted preparation solubility driven optimization antibacterial activity, antibacterial activity sar gram pos bacteria oxazolooxazinone herg inhibition, sodium phosphate prodrug solubility pharmacokinetic and other aspects.Application In Synthesis of (R)-5-(Hydroxymethyl)oxazolidin-2-one

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On May 24, 2004, Pallavicini, Marco; Bolchi, Cristiano; Di Pumpo, Raffaella; Fumagalli, Laura; Moroni, Barbara; Valoti, Ermanno; Demartin, Francesco published an article.Reference of (R)-5-(Hydroxymethyl)oxazolidin-2-one The title of the article was Resolution of 5-hydroxymethyl-2-oxazolidinone by preferential crystallization and investigations on the nature of the racemates of some 2-oxazolidinone derivatives. And the article contained the following:

After ascertaining its conglomerate nature by DSC and solid-state IR analyses, 5-hydroxymethyl-2-oxazolidinone (I), whose enantiomers are very important synthons, was efficiently resolved without chiral auxiliaries by preferential crystallization from a supersaturated isopropanolic solution of (±)-I, slightly enriched in one enantiomer (3.7% ee). Favorable conditions to the entrainment were defined utilizing a previously constructed ternary phase diagram of (R)-I, (S)-I, and 2-propanol. Furthermore, the investigations were extended to other chiral 2-oxazolidinones with a functionalized Me at the 5- or 4-position finding that 5-[(tosyloxy)methyl]-2-oxazolidinone is a racemic compound, whereas just the corresponding mesylate is a conglomerate as the parent alc. I. Interestingly, 4-(hydroxymethyl)-2-oxazolidinone proved to be a racemic compound in contrast with its positional isomer I demonstrating how a relatively fine variation in the mol. structure can unpredictably influence the crystalline nature of the racemate. The X-ray structure determination carried out on (S)-(+)-I, (±)-4-(hydroxymethyl)-2-oxazolidinone and (R)-(+)-4-(hydroxymethyl)-2-oxazolidinone enlightened the importance of the hydrogen bond in determining different supramol. assembling in the two homochiral compounds with respect to the racemic one and allowed a correlation with the stability of the crystal to be made. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).Reference of (R)-5-(Hydroxymethyl)oxazolidin-2-one

The Article related to hydroxymethyl oxazolidinone resolution preferential crystallization, phase diagram hydroxymethyl oxazolidinone resolution preferential crystallization, differential scanning calorimetry hydroxymethyl oxazolidinone resolution preferential crystallization and other aspects.Reference of (R)-5-(Hydroxymethyl)oxazolidin-2-one

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On December 13, 2019, Warner, Christopher J. A.; Berry, Sian S.; Jones, Simon published an article.Synthetic Route of 168297-86-7 The title of the article was Evaluation of bifunctional chiral phosphine oxide catalysts for the asymmetric hydrosilylation of ketimines. And the article contained the following:

A series of hydroxy-functionalized bifunctional phosphine oxides and diphosphine dioxides have been prepared and evaluated as catalysts for the trichlorosilane mediated asym. hydrosilylation of ketimines. Bis-Phosphine oxides, hydroxy-phosphine oxides, and biaryl phosphine oxides all demonstrated good catalytic activity, but poor to moderate enantioselectivity. A bis-P-chiral phosphine oxide (R,R)-Ph(2-MeOC6H4)P(CH2)6PPh(2-MeOC6H4) (32) displayed the highest enantioselectivity of 60%. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Synthetic Route of 168297-86-7

The Article related to phosphine oxide hydroxy chiral preparation organocatalyst asym hydrosilylation ketimine, chiral aromatic amine preparation asym hydrosilylation organocatalyst phosphine oxide, diphosphine oxide phosphorus chiral preparation organocatalyst asym hydrosilylation ketimine and other aspects.Synthetic Route of 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On December 16, 2011, Adams, Harry; Collins, Rebecca C.; Jones, Simon; Warner, Christopher J. A. published an article.Electric Literature of 168297-86-7 The title of the article was Enantioselective preparation of P-chiral phosphine oxides. And the article contained the following:

A highly efficient chiral auxiliary-based strategy for the asym. synthesis of P-chiral phosphine oxides in >98:2 er has been developed. Racemic phosphinyl chlorides undergo highly stereoselective asym. substitution with N-deprotonated chiral oxazolidinones, yielding chiral phosphinic amides, which react with Grignard reagents, giving chiral phosphine oxides. The methodol. involves the highly stereoselective formation of P-chiral oxazolidinones that then undergo displacement with a variety of Grignard reagents to prepare the desired phosphine oxides. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Electric Literature of 168297-86-7

The Article related to phosphine oxide chiral preparation oxazolidinone asym phosphinylation grignard reaction, substitution asym phosphinylation chiral auxiliary oxazolidinone phosphinic amide preparation, arylation alkylation phosphinic amide stereoselective preparation chiral phosphine oxide and other aspects.Electric Literature of 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On October 1, 2010, Lang, Kai; Park, Jongwoo; Hong, Sukwon published an article.COA of Formula: C8H15NO2 The title of the article was Development of Bifunctional Aza-Bis(oxazoline) Copper Catalysts for Enantioselective Henry Reaction. And the article contained the following:

Base-functionalized aza-bis(oxazoline) ligands were prepared to explore the concept of dual activation through the Lewis acid and a tethered tertiary amine base. The catalytic activity of the Cu complex was evaluated for the asym. Henry reaction. Compared with a corresponding unfunctionalized copper complex with external 1-benzyl-4-ethylpiperazine base, the ethylpiperazine-functionalized aza-bis(oxazoline) copper catalyst I resulted in rate acceleration (2.5 times) as well as improved enantioselectivity (72% ee vs 92% ee). The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).COA of Formula: C8H15NO2

The Article related to chiral bifunctional bisoxazoline ligand preparation stereoselective henry reaction catalyst, aryl aldehyde copper chiral base functionalized ligand henry reaction, benzylic alc nitro derivative stereoselective preparation, henry reaction kinetic copper ligand base reaction order and other aspects.COA of Formula: C8H15NO2

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On July 31, 2010, Bourcet, Emmanuel; Fache, Fabienne; Piva, Olivier published an article.Safety of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one The title of the article was Stereocontrolled Synthesis of the Highly Functionalized Core Structure of Aurisides by Ring-Closing Metathesis. And the article contained the following:

Two approaches based on the ring-closing metathesis reaction have been explored for the synthesis of the core structure I of the marine natural products, the aurisides. The second approach, accomplished in a stereocontrolled manner, used both a Brown’s allylation and an Evans’ aldolization, and finally a transannular ketalization to deliver a highly functionalized auriside analog. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Safety of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

The Article related to auriside core structure stereocontrolled synthesis ring closing metathesis, allylation brown stereocontrolled synthesis auriside core structure, evans aldolization stereocontrolled synthesis auriside core structure, transannular ketalization stereocontrolled synthesis auriside core structure and other aspects.Safety of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On March 24, 2000, Fukuzawa, Shin-ichi; Matsuzawa, Hiroshi; Yoshimitsu, Shin-ichi published an article.Recommanded Product: (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one The title of the article was Asymmetric Samarium-Reformatsky Reaction of Chiral α-Bromoacetyl-2-oxazolidinones with Aldehydes. And the article contained the following:

The samarium(II) iodide mediated asym. Reformatskii-type reaction of chiral bromoacetyloxazolidinones I (R = Me2CH, Ph, PhCH2; R1 = H, Me, Ph) with various aldehydes R2CHO [R2 = Me2CH, Et2CH, c-C6H11, Me3C, Me(CH2)6, PhCH2CH2, Ph] was studied. A series of chiral 4-substituted 2-oxazolidinones and 5,5-disubstituted “SuperQuat” oxazolidinones were employed as chiral auxiliaries for α-bromoacetic acid. The reaction of I (R = Me2CH; R1 = H) with aldehydes R2CHO [R2 = Me2CH, Et2CH, c-C6H11, Me3C, Me(CH2)6, PhCH2CH2, Ph] gave β-hydroxy carboximides II [R = H; R1 = Me2CH; R2 = Me2CH, Et2CH, c-C6H11, Me3C, Me(CH2)6, PhCH2CH2, Ph] in 67-92% yields and in 64-99% diastereomeric excess. The majority of the reaction product derived from I (R = Me2CH; R1 = Ph) were highly crystalline; a single recrystallization of II [R = Me2CH; R1 = Ph; R2 = Me2CH, Me3C, Me(CH2)6, Ph] gave diastereomerically pure products with the β-hydroxy epimer not detectable by spectroscopic methods. The absolute configurations of the β-hydroxy carboximides were determined by comparison of the optical rotations of the corresponding known Et esters to the literature values. Hydrolytic cleavage of the appended β-hydroxy moieties from the auxiliary SuperQuats derivatives II (R = Me2CH; R1 = Me, Ph) was readily achieved under mild conditions using lithium hydroxide; the corresponding carboxylic acids and the returned SuperQuats were obtained in good yields without any evidence of racemization. The absolute configuration of the adduct derived from benzaldehyde was found to be R, with the samarium enolate formed by reduction of the bromoacetyl derivative favoring the transition state predicted from chelation control of the reagent; this is in analogy to the discussion that has been used for the corresponding titanium enolate. The stereochem. of the reaction may be explained by incorporating the Nerz-Stormes-Thornton chair transition structure model. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Recommanded Product: (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

The Article related to hydroxy acid nonracemic stereoselective preparation, ester beta hydroxy stereoselective preparation, hydroxyalkanoyl oxazolidinone stereoselective preparation, asym reformatskii reaction bromoacetyl oxazolidinone aldehyde, stereoselective reformatskii reaction bromoacetyl oxazolidinone aldehyde and other aspects.Recommanded Product: (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Tomas, Loic; Boije af Gennaes, Gustav; Hiebel, Marie Aude; Hampson, Peter; Gueyrard, David; Pelotier, Beatrice; Yli-Kauhaluoma, Jari; Piva, Olivier; Lord, Janet M.; Goekjian, Peter G. published an article in 2012, the title of the article was Total Synthesis of Bistramide A and Its 36(Z) Isomers: Differential Effect on Cell Division, Differentiation, and Apoptosis.Recommanded Product: 168297-86-7 And the article contains the following content:

The total synthesis of bistramide A and its 36(Z),39(S) and 36(Z),39(R) isomers shows that these compounds have different effects on cell division and apoptosis. The synthesis relies on a novel enol ether-forming reaction for the spiroketal fragment, a kinetic oxa-Michael cyclization reaction for the tetrahydropyran fragment, and an asym. crotonylation reaction for the amino acid fragment. Preliminary biol. studies show a distinct pattern of influence of each of the three compounds on cell division, differentiation, and apoptosis in HL-60 cells, thus suggesting that these effects are independent activities of the natural product. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Recommanded Product: 168297-86-7

The Article related to bistramide a isomer preparation antitumor, cell division differentiation apoptosis differential effect bistramide a, enol ether formation total synthesis bistramide a isomer, kinetic oxa michal cyclization total synthesis bistramide a isomer, asym crotonylation total synthesis bistramide a isomer and other aspects.Recommanded Product: 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On October 28, 2004, Burke, Martin D.; Berger, Eric M.; Kwon, Ohyun; Park, Seung Bum; Schreiber, Stuart L. published a patent.Safety of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one The title of the patent was Generation of skeletal diversity within a combinatorial library. And the patent contained the following:

The present invention provides a method of synthesizing a library of chem. compounds with skeletal diversity. Two approaches are used to create skeletal diversity within a library of chem. compounds: (1) the “”branching pathways”” (or reagent-based) approach; and (2) the “”folding pathways”” (or substrate-based) approach. Upon exposure to certain reaction conditions the members of the library undergo unique transformations into a diverse collection of mol. skeletons, which can be functionalized and derivatized further to generate a large collection of unique, natural product-like compounds A furan-based library synthesized using the folding pathways approach is provided, and a polycyclic library created using the branching pathways approach is also provided. The invention also provides materials, reagents, intermediates, and kits useful in the practice of the inventive method as well as method for screening the inventive compounds The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Safety of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

The Article related to oxazolidinone combinatorial library stereoselective preparation solid phase synthesis, split pool synthesis skeletal diversity combinatorial chem oxazolidinone preparation, combinatorial matrix mol skeleton furan derivatization, skeletal diversity branched diels alder polycyclic combinatorial library and other aspects.Safety of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On January 10, 2008, Ryono, Dennis E.; Cheng, Peter T. W.; Bolton, Scott A.; Chen, Sean S.; Shi, Yan; Meng, Wei; Tino, Joseph A.; Zhang, Hao; Sulsky, Richard B. published a patent.Category: oxazolidine The title of the patent was Novel N-heterocyclic phosphonates and phosphinates as glucokinase activators for treatment of Type II diabetes. And the patent contained the following:

Nitrogen heterocyclic phosphorus amidoesters Y-XCONH(QR4R5R6) [1; Q = optionally substituted 2-N-heterocyclyl; R4 = optionally (5-7-membered heterocyclic) ω-phosphonoalkyl, ω-[(organyloxy)phosphinyl]alkyl, ω-phosphonatoalkyl, ω-phosphinatoalkyl, ω-phosphinylalkyl; R5, R6 = H, alkyl, halo, carboxy; X = substituted methylene, imino, vinylidene, cyclopropylidene, N-heterocyclic group, imidazolylmethyl, isoindolylmethyl, 3-indolylmethyl; Y = (hetero)aralkyl, (hetero)aryl, H], useful as activators of mice and human glucokinase for treatment of Type II diabetes, were prepared by combination of amidation, phosphonylation, alkylation, esterification and heterocyclization reactions of suitable precursors. Preferably, the compounds 1 have the structure of RXCONHQ1X1P(O)R2R3 [R = iPr, 4-MeSO2C6H4, 4-(cyclopropylsulfonyl)phenyl, PhCH2CHMe, PhCH2CH2, 5-(methylsulfonyl)-2-pyrazinyl, 1-(methylsulfonyl)-4-piperidinyl, 5-(1-azetidinylcarbonyl)-2-pyrazinyl; X = 2-cyclopentylethylidene, 4-tetrahydropyranyl-2-ethylidene, 5-(MeOCH2CHMeO)-1,3-OC6H3, 5-(iPrO)-1,3-OC6H3, 5-(1-pyrrolidinylcarbonyl)-1,3-OC6H3, 5-(2-pyridinyloxy)-1,3-OC6H3, 5-(2-pyrimidinyloxy)-1,3-OC6H3, 5-(2-pyrazinyloxy)-1,3-OC6H3; Q1 = 2-thiazol-5-yl, 2-pyridin-5-yl, 2-pyrazin-5-yl, 2-thiazol-4-yl, 2-pyridin-6-yl, 3-pyrazol-1-yl; X1 = bond, CH2, CH2CH2, CH:CH; R2 = R3 = OEt, OMe, OiPr; R3 = OEt, R4 = Me; X1P(O)R3R4 = CH2OP(O)Me2; P(O)R3P4 = 2-oxo-1,3,2-dioxaphosphorin-2-yl]. The prepared compounds 1 were tested in vitro for glucokinase activation and in vivo in diet-induced obese mice for oral glucose tolerance. In an example, amidothiazolylmethyl-substituted cyclic phosphonate, 2-RCH2-2-oxo-1,3,2-dioxaphosphorinane [169, R = 2-[4-MeSO2C6H4[5-(MeOCH2CHMeO)-1,3-OC6H3CONH]-thiazol-4-yl]] was prepared by heterocyclization of 2-BocNH-thiazol-4-ylmethylphosphonic acid bis(trimethylsilyl) ester with 1,3-propanediol, followed by deprotection and coupling with 3-[(1S)-2-methoxy-1-methylethoxy]-5-(4-methylsulfonylphenoxy)benzoic acid with 28% yield. In another example, the compound 169 exhibited 50% activation of human glucokinase at 12 mM of glucose at concentration (EC50) of 9 nM. The compounds of the invention also caused 62-80% reduction in glucose AUC level in diet-induced obese (DIO) mice at 30 mg/kg dose by oral administration. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).Category: oxazolidine

The Article related to phosphonate phosphinate heterocyclic pyridinyl pyrazinyl thiazolyl preparation glucokinase activator, benzeneacetamide pyridinyl thiazolyl pyrazinyl phosphonate phosphinate preparation glucokinase activator, diabetes treatment glucokinase activator heterocyclic sulfonyl benzeneacetamide phosphonate phosphinate and other aspects.Category: oxazolidine

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem