Category: 104322-63-6

Davis, Franklin A.; Lal, G. Sankar; Wei, Jia published the artcile< Stereo- and regioselective formation of silyl enol ethers via oxidation of vinyl anions>, Electric Literature of 104322-63-6, the main research area is silyl enol ether stereoselective preparation; oxidation vinyl bromide derivative stereoselective; vinyllithium stereoselective oxidation.

Oxidation of E- and Z-vinyllithiums, R1CR2:CR3Li (R1-R3 = Ph, Me, Et, etc.), with silyl peroxides, RSiMe2OOSiMe2R (R = Me, Me3C), affords silyl enol ethers, R1CR2:CR3OSiMe2R, in good to excellent yield with retention of configuration. This methodol. represents a useful new procedure for the stereo- and regioselective synthesis of ketone enolates.

Tetrahedron Letters published new progress about Oxidation, stereoselective. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Electric Literature of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Davis, Franklin A.; Towson, James C.; Weismiller, Michael C.; Lal, Sankar; Carroll, Patrick J. published the artcile< Chemistry of oxaziridines. 11. (Camphorylsulfonyl)oxaziridine: synthesis and properties>, Recommanded Product: (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide, the main research area is camphorylsulfonyloxaziridine preparation oxidation sulfide; crystal structure camphorylsulfonyloxaziridine; mol structure camphorylsulfonyloxaziridine; oxaziridine camphorylsulfonyl preparation crystal structure; asym synthesis sulfoxide.

(+)- And (-)-(camphorylsulfonyl)oxaziridines (+)- and (-)-I are prepared in 3 steps from (+)- and (-)-camphorsulfonyl chlorides in 67% overall yield. In contrast to other optically active sulfonimines, which give on oxidation mixtures of oxaziridine diastereoisomers, oxidation of camphorsulfonimine (-)-II [the precursor to (+)-I] with oxone produces only a single isomer in >95% yield. In the asym. oxidation of prochiral sulfides by I the enantioselectivities are lower than those reported for oxidation by optically active N-sulfamyloxaziridine (5-73 vs. 35-60% enantiomeric excess). This difference is discussed in terms of different active site structures for the 2 oxaziridines. The configuration of the oxaziridine 3-membered ring in I controls the configuration of the product, with (+)-I and (-)-I giving the opposite senses of asym. induction. I does not readily oxidize amines or epoxidize alkenes. Oppolzer’s sultam chiral auxiliary [(-)-III] is prepared in 92% yield by hydride reduction of (-)-II. The structure of (+)-I was determined by x-ray crystallog.

Journal of the American Chemical Society published new progress about Crystal structure. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Recommanded Product: (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Davis, Franklin A.; Kumar, Anil published the artcile< Kinetic resolution in the asymmetric hydroxylation of enolates. Stereospecific synthesis of (2S,3R)-(-)-verrucarinolactone>, Recommanded Product: (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide, the main research area is methylvalerolactone asym hydroxylation camphorylsulfonyloxaziridine; verrucarinolactone stereoselective preparation.

Asym. hydroxylation of (±)-3-methylvalerolactone (I; R = H) with substoichiometric amounts of the (-)-(camphorylsulfonyl)oxaziridine affords (2S,3R)-(-)-verrucarinolactone (I; R = HO) in 60% ee, which on crystallization is obtained enantiomerically pure. This result not only represents a highly efficient stereospecific synthesis of an important lactone, but also demonstrates the application of kinetic resolution and asym. hydroxylation in the synthesis of enantiomerically enriched α-hydroxy carbonyl compounds having multiple stereocenters.

Journal of Organic Chemistry published new progress about 104322-63-6. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Recommanded Product: (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Wei, Yen; Bakthavatchalam, R.; Jin, Xian Ming; Murphy, Christopher K.; Davis, Franklin A. published the artcile< Effect of aggregation on stereochemistry and mechanism of asymmetric oxidation of the lithium enolate of methyl 3,3-dimethylbutanoate in the solid state and in solution>, Name: (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide, the main research area is asym oxidation lithium enolate mechanism; enantiopure camphorylsulfonyloxaziridine oxidation lithium enolate; stereoselective oxidation lithium enolate; solid state oxidation lithium enolate.

Oxidation of the title enolate by enantiopure (camphorylsulfonyl)oxaziridines in THF afforded α-hydroxy ester with 53-73% ee, but the product from the solid state reactions was racemic. The results suggest that the enolate exists and reacts as an aggregate in the solid state reactions.

Tetrahedron Letters published new progress about Oxidation. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Name: (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Davies, Stephen G.; Foster, Emma M.; Lee, James A.; Roberts, Paul M.; Thomson, James E. published the artcile< Stereospecific Cyclization Strategies for α,ε-Dihydroxy-β-amino Esters: Asymmetric Syntheses of Imino and Amino Sugars>, Quality Control of 104322-63-6, the main research area is amino acid alditol imino preparation stereoselective cyclization camphorsulfonyl oxaziridine.

A range of biol. significant imino and amino sugars [1,4-dideoxy-1,4-imino-D-allitol, 3,6-dideoxy-3,6-imino-L-allonic acid, (3R,4S)-3,4-dihydroxy-L-proline, 1,5-anhydro-4-deoxy-4-amino-D-glucitol, and 1,5-anhydro-4-deoxy-4-amino-L-iditol] has been prepared via stereospecific cyclization of α,ε-dihydroxy-β-amino esters. These substrates are readily prepared via conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide to enantiopure α,β-unsaturated esters (β-substituted with cis- and trans-dioxolane units) coupled with in situ enolate oxidation with camphorsulfonyl-oxaziridine (CSO). Activation of the ε-hydroxyl group allowed cyclization to either the corresponding pyrrolidine or the tetrahydropyran scaffold, with the course of the cyclization process being dictated by the relative configuration of the dioxolane unit. When the α,ε-dihydroxy-β-amino ester bears a cis-dioxolane unit, cyclization occurs upon attack of the β-amino substituent to give the corresponding pyrrolidine after in situ N-debenzylation. In contrast, when the α,ε-dihydroxy-β-amino ester bears a trans-dioxolane unit, cyclization occurs upon attack of the α-hydroxyl substituent to give the corresponding tetrahydropyran.

Journal of Organic Chemistry published new progress about Alditols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Quality Control of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Abraham, Elin; Candela-Lena, Jose I.; Davies, Stephen G.; Georgiou, Matthew; Nicholson, Rebecca L.; Roberts, Paul M.; Russell, Angela J.; Sanchez-Fernandez, Elena M.; Smith, Andrew D.; Thomson, James E. published the artcile< Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer>, HPLC of Formula: 104322-63-6, the main research area is phytosphingosine jaspine B pachastrissamine amino alc asym preparation; ester unsaturated stereoselective conjugate addition oxidation intramol cyclization.

The highly diastereoselective conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide to a γ-silyloxy-α,β-unsaturated ester and in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine has been used as the key step in the asym. synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine I, jaspine B (pachastrissamine) II and its C(2)-epimer III.

Tetrahedron: Asymmetry published new progress about Amino alcohols, chiral Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, HPLC of Formula: 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Foy, Hayden C.; Schwan, Adrian L.; Dudding, Travis published the artcile< A mechanistic study of oxygen atom transfer from N-sulfonyloxaziridine to enolates>, Recommanded Product: (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide, the main research area is enolate sulfonyloxaziridine oxidation reaction mechanism free energy.

Enolate additions to chiral N-sulfonyloxaziridines providing enantiomerically enriched α-hydroxy carbonyl compounds is a reaction of importance, yet a clear understanding of the factors governing stereoinduction in these transformations remains ambiguous. This is despite, previous computational studies, one by Bach et al. employing truncated model systems exploring oxygen atom transfer to an unsubstituted lithium enolate and another by our own group. In clarifying this reactivity we report here a computational study examining oxygen atom transfer from 1-S-(+)-(10-camphorsulfonyl)oxaziridine, viz., archetypal Davis chiral oxaziridine to substituted Li, Na, K enolates offering improved mechanistic understanding. From this investigation, a revised model is offered revealing the metal cation, chelation effects and sterics as decisive stereocontrolling factors in enolate additions to chiral N-sulfonyloxaziridines affording enantiomerically enriched α-hydroxy carbonyl compounds

Tetrahedron published new progress about Bader electron density. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Recommanded Product: (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Peng, Yu; Luo, Zhen-Biao; Zhang, Jian-Jian; Luo, Long; Wang, Ya-Wen published the artcile< Collective synthesis of several 2,7'-cyclolignans and their correlation by chemical transformations>, Recommanded Product: (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide, the main research area is stereoselective cyclization aristoligone aristoligol preparation; cyclolignan cyclogalgravin linchpin redox neolignan kadangustin plant cyclization.

Collective synthesis of antimalarial 2,7′-cyclolignans has been stereoselectively achieved employing (±)-cyclogalgravin as a linchpin through a series of functional group conversions, including redox reactions. Interestingly, (±)-cyclogalgravin can be correlated with the neolignan (±)-kadangustin J isolated from a different plant source, through a highly efficient dehydrative cyclization reaction with excellent diastereotopic differentiation of the veratryl group and concomitant construction of the C1-C7 bond. It is noteworthy that the first total synthesis of stereo-divergent (±)-8,8′-epi-aristoligone, (±)-8′-epi-aristoligone, (±)-8′-epi-8-OH-aristoligone, and (±)-8′-epi-aristoligol was demonstrated.

Organic & Biomolecular Chemistry published new progress about Cyclization, stereoselective. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Recommanded Product: (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Hewawasam, Piyasena; Meanwell, Nicholas A.; Gribkoff, Valentin K.; Dworetzky, Steven I.; Boissard, Christopher G. published the artcile< Discovery of a novel class of BK channel openers: enantiospecific synthesis and BK channel opening activity of 3-(5-chloro-2-hydroxyphenyl)-1,3-dihydro-3-hydroxy-6-(trifluoromethyl)-2H-indol-2-ones>, Related Products of 104322-63-6, the main research area is indolone hydroxy hydroxyphenyl preparation BK channel; BK channel opener hydroxyindolone hydroxyphenyl derivative; structure activity hydroxyphenylindolone BK channel openers.

3-Aryl-3-hydroxyindol-2-ones have been identified as a novel class of BK channel openers. Synthesis of both racemic and chiral 3-aryl-3-hydroxyindolones is described along with their electrophysiol. evaluation as activators of the cloned BK channel mSlo expressed in Xenopus laevis oocytes. The preliminary SAR data indicate the importance of both an electron-withdrawing substituent on the oxindole nucleus and the phenolic hydroxyl for expression of BK channel opening properties. Moreover, the dependence of BK channel opening activity on the absolute configuration of the chiral center in this pharmacophore has been demonstrated.

Bioorganic & Medicinal Chemistry Letters published new progress about Potassium channel openers (BK). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Related Products of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Jadhav, Hemsagar P.; Pathare, Dnyandeo B. published the artcile< Separation and determination of the S-isomer of (10-camphorsulfonyl) oxaziridine in a bulk drug substance by normal-phase liquid chromatography>, Application of C10H15NO3S, the main research area is oxaziridine bulk drug substance normal phase liquid chromatog.

Objective: To develop novel, simple and accurate enantiomeric separation of (10-Camphorsulfonyl) oxaziridine by normal-phase high-performance liquid chromatog. method as per ICH guidelines. Methods: The S-isomer and R-isomer of (10-Camphorsulfonyl) oxaziridine were baseline resolved on a Chiralcel OD-H (250 x 4.0 mm i. d, 5 μm) column using a mobile phase system containing n-Hexane: ethanol: trifluoroacetic acid (90:10:0.1 volume/volume/v.) at detector wavelength 210 nm and column temperature 30 °C. The chromatog. resolutions between S-isomer and R-isomer were found three. The developed method was extensively validated according to ICH guidelines. Results: Good linearity was observed for S-isomer over the concentration range of 900-9000 ng/mL, with the linear regression (Correlation coefficient R = 0.999) and proved to be robust. The limit of detection and limit of quantification of S-isomer was found to be 400 and 900 ng/mL, resp. for 20 μl injection volume The percentage recovery of S-isomer was ranged from 97.0 to 102.0 in bulk drug samples of (10-Camphorsulfonyl) oxaziridine. (10-Camphorsulfonyl) oxaziridine sample solution and mobile, phase was found to be stable for at least 48 h. The proposed method was found to be suitable and accurate for the quant. determination of S-isomer in bulk drugs. Conclusion: A novel, simple and accurate normal phase LC method was described for the enantiomeric separation of 10-Camphorsulfonyl Oxaziridine is precise and specific.

International Journal of Pharmacy and Pharmaceutical Sciences published new progress about Drug delivery systems. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Application of C10H15NO3S.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com