Category: isothiazole

Davis, Franklin A.; Kumar, Anil published the artcile< Kinetic resolution in the asymmetric hydroxylation of enolates. Stereospecific synthesis of (2S,3R)-(-)-verrucarinolactone>, Application of C10H15NO3S, 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, Application of C10H15NO3S.

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>, 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 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, 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

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>, Product Details of C10H15NO3S, 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, Product Details of C10H15NO3S.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Escalante, Jaime; Juaristi, Eusebio published the artcile< Enantioselective synthesis of β-amino acids. 6. High 1,2-stereoinduction in the preparation of enantiopure 2(R)-hydroxy-3(R)-N-benzoylamino-3-phenylpropionic acid (like stereoisomer of Taxol's side chain)>, Quality Control of 104322-63-6, the main research area is stereoselective hydroxylation phenylperhydropyrimidinone camphor oxaziridine; pyrimidinone phenylperhydro stereoselective hydroxylation oxaziridine; asym synthesis phenylisoserine.

The remarkably high 1,2-stereoinduction encountered in the hydroxylation of 6(S)-phenylperhydropyrimidin-4-one I allows for the preparation of enantiopure N-benzoyl (2R,3R)-3-phenylisoserine (II), the like stereoisomer of taxol’s C-13 side chain.

Tetrahedron Letterspublished new progress about Amino acids, hydroxy Role: SPN (Synthetic Preparation), 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

Davis, Franklin A.; Reddy, R. Thimma; Reddy, Rajarathnam E. published the artcile< Asymmetric synthesis of sulfinimines: applications to the synthesis of nonracemic β-amino acids and α-hydroxyl β-amino acids>, Safety of (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 synthesis sulfinimine; beta amino acid; hydroxy beta amino acid; stereoselective oxidation sulfenimine dichlorocamphoryloxaziridine; chlorocamphoryloxaziridine stereoselective oxidation sulfenimine; camphoryloxaziridine dichloro stereoselective oxidation sulfenimine; oxaziridine dichlorocamphoryl stereoselective oxidation sulfenimine.

Asym. oxidation of sulfenimines I (Ar = Ph, R = H, X = H, MeO; Ar = p-tolyl, R = Me, X = H) with chiral oxaziridines II or III affords sulfinimines IV or V (88-90% ee), which are chiral ammonia imine synthons useful in the enantioselective synthesis of β-amino acids and α-hydroxy β-amino acids such as the C-13 side chain of taxol.

Journal of Organic Chemistrypublished new progress about Amino acids, hydroxy Role: SPN (Synthetic Preparation), PREP (Preparation). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Safety of (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

Mahale, Rajendra D.; Rajput, Mahesh R.; Maikap, Golak C.; Gurjar, Mukund K. published the artcile< Davis Oxaziridine-Mediated Asymmetric Synthesis of Proton Pump Inhibitors Using DBU Salt of Prochiral Sulfide>, Formula: C10H15NO3S, the main research area is camphorsulfonyl oxaziridine asym sulfoxidation sulfide omeprazole PPI preparation.

A simple and clean asym. synthesis of proton pump inhibitors using inexpensive 10-camphorsulfonyl oxaziridine is described. The activation of prochiral sulfide is based on use of the DBU salt which is capable of enhancing the reactivity and enantioselectivity.

Organic Process Research & Developmentpublished new progress about Enantioselective synthesis. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Formula: C10H15NO3S.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Davis, Franklin A.; Wei, Jia; Sheppard, Aurelia C.; Gubernick, Steven published the artcile< The mechanism of hydroxylation of organometallic reagents by 2-sulfonyloxaziridines>, Reference of 104322-63-6, the main research area is hydroxylation organometallic sulfonyloxaziridine mechanism; phenol octanol cresol.

The hydroxylation of organometallic reagents (e.g. PhMgBr) by 2-sulfonyloxaziridines (e.g. I) is shown to involve a hemiaminal intermediate, whose stability is apparently related to the nucleophilicity of the hydroxylated product (e.g. PhOH).

Tetrahedron Letterspublished new progress about Grignard reagents Role: RCT (Reactant), RACT (Reactant or Reagent). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Reference of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Dowden, James; Moreau, Christelle; Brown, Richard S.; Berridge, Georgina; Galione, Antony; Potter, Barry V. L. published the artcile< Chemical synthesis of the second messenger nicotinic acid and adenine dinucleoside phosphate by total synthesis of nicotinamide adenine dinucleotide phosphate>, Application of C10H15NO3S, the main research area is second messenger nicotinamide adenine nucleotide oligoribonucleotide preparation calcium release; nicotinic acid adenine nucleotide nicotinamide preparation calcium release NADP.

The first single-isomer synthesis of NADP is reported. Installation and maintenance of sensitive phosphate and pyridinium functionalities were key to success. Significantly, conversion of NADP into the important mammalian second messenger nicotinic acid adenine dinucleotide phosphate (NAADP) was achieved. The biol. evaluation of the activity of the release of Ca2+ ions confirms the identity of NAADP. Ca2+ release properties against sea-urchin-egg homogenate and spectroscopic characterization are reported.

Angewandte Chemie, International Editionpublished new progress about Calcium release channels Role: BCP (Biochemical Process), BSU (Biological Study, Unclassified), BIOL (Biological Study), PROC (Process). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Application of C10H15NO3S.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Oka, Natsuhisa; Morita, Yasuhiro; Itakura, Yuta; Ando, Kaori published the artcile< Synthesis of inosine 6-phosphate diesters via phosphitylation of the carbonyl oxygen>, 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 nucleoside inosine phosphate diester synthesis phosphitylation phosphoramidite acidic catalyst.

Inosine derivatives bearing a phosphodiester group at the O6-position of the nucleobase were synthesized via phosphitylation of the carbonyl oxygen using phosphoramidites activated by non-nucleophilic acidic activators such as N-(cyanomethyl)pyrrolidinium triflate.

Chemical Communications (Cambridge, United Kingdom)published new progress about Nucleosides 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, 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