Heterocyclic Building Blocks-Oxazolidine

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

On December 3, 2020, Sebhat, Iyassu; He, Shuwen published a patent.Formula: C8H15NO2 The title of the patent was Preparation of 3-cyclopropyl-3-(3-acyloxyphenyl)propanoic acid derivatives as Gpr40 agonists. And the patent contained the following:

The compounds represented by formula I [Z = C(O)OH, C(O)OR5, C(O)NHR6, C(O)NHS(O)2R5, S(O)2NHC(O)R5, P(O)(R5)OR6, P(O)(OR6)2, S(O)2OR6; or Z = (un)substituted 4- or 5-membered heterocycle; R5 = each (un)substituted C1-6 alkyl, C3-6 cycloalkyl, Ph, or phenyl-C1-6 alkyl; R6 = hydrogen or each (un)substituted C1-6 alkyl, C3-6 cycloalkyl, Ph, or phenyl-C1-6 alkyl; R1, R2, R3, R4 = each independently hydrogen, halogen, OH, or each (un)substituted C1-6 alkyloxy, C1-6 alkyl, C3-6 cycloalkyl, or 3- to 6-membered heterocycloalkyl; Y1, Y2, Y3, or Y4 = each independently N, CH, or CRY; each RY = independently halogen, cyano, OH, NH2, or each (un)substituted C1-6 alkoxy, NH-(C1-6 alkyl), N-(C1-6 alkyl)2, C1-6 alkyl, C3-6 cycloalkyl, or 3- to 6-membered heterocycloalkyl; L1 = *-OC(O)-, or *-C(O)O-, wherein * represents the connection to Ring B; Ring B = each (un)substituted arylene, heteroarylene, C3-10 cycloalkylene, or 3- to 10-membered heterocycloalkylene; L2 = a bond or each (un)substituted C1-6 alkylene, or -(C1-6 alkylene)-O-] or pharmaceutically acceptable salts, solvates, stereoisomers, or prodrugs thereof are prepared The compounds I are gut-restricted compounds and full or partial G protein-coupled receptor 40 (GPR40) agonists and useful for the treatment of conditions or disorders involving the gut-brain axis. The conditions or disorder is (1) a metabolic disorder such as type 2 diabetes, hyperglycemia, metabolic syndrome, obesity, hypercholesterolemia, nonalcoholic steatohepatitis, or hypertension or (2) a nutritional disorder such as short bowel syndrome, intestinal failure, or intestinal insufficiency. Thus, a solution of 0.28 g 3-[(diisopropylamino)methyl]-4-(5-fluoro-2-methoxypyridin-4-yl)benzoic acid and 0.13 g Me (S)-3-cyclopropyl-3-(3-hydroxyphenyl)propanoate in 3 mL CH2Cl2 was treated with 35 mg 4-dimethylaminopyridine and 0.18 g DCC and stirred at 25° for 16 h to give, after workup and purification using preparative TLC, (S)-3-cyclopropyl-3-[3-[[3-[(diisopropylamino)methyl]-4-(5-fluoro-2-methoxypyridin-4-yl)benzoyl]oxy]phenyl]propanoic acid (II). II showed an agonist activity with EC50 of ≤10 nM in a human GPR40 assay. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Formula: C8H15NO2

The Article related to acyloxyphenylcyclopropylpropanoic acid preparation gpr40 agonist, metabolic disorder type 2 diabetes treatment gpr40 agonist preparation, hyperglycemia metabolic syndrome obesity treatment gpr40 agonist preparation, hypercholesterolemia nonalcoholic steatohepatitis hypertension treatment gpr40 agonist preparation and other aspects.Formula: C8H15NO2

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On January 6, 2017, Sagawa, Naoya; Sato, Haruka; Hosokawa, Seijiro published an article.Computed Properties of 168297-86-7 The title of the article was Remote Asymmetric Induction Using Acetate-Type Vinylketene Silyl N,O-Acetals. And the article contained the following:

Remote asym. induction by the vinylogous Mukaiyama aldol reaction using the acetate-type vinylketene silyl N,O-acetal possessing a chiral auxiliary was achieved. The silyl N,O-acetal derived from crotonate and L-valine afforded the O-silylated 5R- and 5S-adducts selectively by treatment with SnCl4 and BF3·OEt2, resp. The SnCl4-mediated isomerization of silyl dienol ether was found, and the resulting major isomer showed high reactivity to give γ-adduct in high stereoselectivity. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Computed Properties of 168297-86-7

The Article related to remote asym induction acetate vinylketene silyl nitrogen oxygen acetal, crystal structure oxazolidinone vinylketene silyl acetal hydroxyoxoalkenyl preparation asym, mol structure oxazolidinone vinylketene silyl acetal hydroxyoxoalkenyl preparation asym, aldehyde asym induction remote mukaiyama aldol vinylketene silyl acetal and other aspects.Computed Properties of 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On September 16, 2016, Brun, Elodie; Bellosta, Veronique; Cossy, Janine published an article.Electric Literature of 168297-86-7 The title of the article was Synthesis of the Acyclic Carbon Skeleton of Filipin III. And the article contained the following:

The synthesis of the carbon skeleton I of filipin III (II), a polyenic macrolactone possessing 11 stereogenic centers, has been achieved using a convergent strategy with a longest linear sequence of 19 steps starting from hexanal. The construction of the polyene has been realized by using two successive Heck couplings as the key steps. The control of the stereogenic centers of the polyol fragment has been performed by utilizing an Evans aldolization, a 1,3-syn aldolization, enantio- and diastereoselective allylations, an hemiacetalization/oxa-Michael sequence and a 1,3-syn reduction The polyol and polyenic fragments have been coupled using a 1,5-anti diastereoselective aldolization followed by a 1,3-anti reduction 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 filipin iii acyclic carbon skeleton preparation convergent strategy, hexanal synthon filipin iii acyclic carbon skeleton, successive heck coupling reaction filipin iii synthesis, aldolization evans syn anti filipin iii synthesis, enantioselective allylation filipin iii synthesis, diastereoselective allylation filipin iii synthesis and other aspects.Electric Literature of 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On March 7, 2002, Sciotti, Richard J.; Djuric, Steven W.; Pliushchev, Marina published a patent.HPLC of Formula: 97859-49-9 The title of the patent was Preparation of oxazolidinone chemotherapeutic agents. And the patent contained the following:

Compounds of the formula I [A = Ph, substituted five-membered aromatic ring containing 1 or 2 atoms selected from N, O, and S and the remaining atoms are carbon, or substituted 6-membered aromatic ring containing 1 or 2 nitrogen atoms and the remaining atoms are carbon; R1, R2 = independently H, alkyl, cycloalkyl, hydroxy, amino, halo, haloalkyl, and perfluoroalkyl; R3 = optionally substituted alkyl, alkanoyl, carboxamido, cycloalkyl, cyclothioalkoxy, etc.; R4 = substituted N, O, or S] or therapeutically acceptable salts or prodrugs thereof were prepared Thus, Me 4-((4-((5S)-5-((acetylamino)methyl)-2-oxo-1,3-oxazolidin-3-yl)-2-fluorophenyl)ethynyl)benzoate (II) was synthesized in 6 steps from (5R)-5-(hydroxymethyl)-1,3-oxazolidin-2-one (III). Oxazolidinones of formula I are useful for treating bacterial infections, psoriasis, arthritis, and toxicity due to chemotherapy. Preparation of the compounds, compositions containing the compounds, and treatment of diseases using the compounds are disclosed. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).HPLC of Formula: 97859-49-9

The Article related to oxazolidinone chemotherapeutic agent asym synthesis chemotherapy toxicity treatment method, psoriasis treatment method oxazolidinone chemotherapeutic agent asym synthesis, arthritis treatment method oxazolidinone chemotherapeutic agent asym synthesis, bacterial infection treatment method oxazolidinone chemotherapeutic agent asym synthesis and other aspects.HPLC of Formula: 97859-49-9

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem