Day: October 12, 2022

Davis, Franklin A.; Reddy, G. Venkat; Chen, Bang-Chi; Kumar, Anil; Haque, M. Serajul published the artcile< Enantioselective Synthesis of 2-Methyl-2-hydroxy-γ-butyrolactone and Its Application in the Asymmetric Synthesis of Frontalin and Mevalonolactone>, COA of Formula: C10H15NO3S, the main research area is asym hydroxylation methylbutyrolactone phenylisobutyrate; camphorsulfonyloxaziridine chiral auxiliary hydroxylation; frontalin formal asym synthesis; mevalonolactone asym synthesis.

The asym. hydroxylation of the enolates of (R)-menthyl 2-methyl-3-phenylpropionate (I) and 2-methyl-γ-butyrolactone (II) with (camphorylsulfonyl)oxaziridines was studied. The stereoselectivities of the tertiary α-hydroxy carbonyl products were highly dependent on the enolate structure, the oxidizing reagents, and the reaction conditions. While high diastereoselectivity (up to 94%) was obtained for enolates of I with substoichiometric amounts of (camphorylsulfonyl)oxaziridine, the yields were unsatisfactory. On the other hand, the enantioselective α-hydroxylation of the sodium enolate of II with [(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine afforded α-hydroxy lactone in 70% yield and 84% ee. The enantiomeric excess was improved to >93% ee by crystallization of the corresponding benzoate. The utility of both enantiomers of the benzoate was demonstrated in the formal asym. synthesis of (1S,5R)-(-)-frontalin and in the asym. synthesis of (R)-(-)-mevalonolactone.

Journal of Organic Chemistry published new progress about Chiral synthons. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, COA of Formula: C10H15NO3S.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Polywka, Mario E. C. published the artcile< Camphor based auxiliaries for asymmetric synthesis>, Category: isothiazole, the main research area is camphor chiral auxiliary asym synthesis review; bornanesultam chiral auxiliary review; oxaziridine camphorsulfonyl chiral auxiliary review.

A review of chiral auxiliaries, e.g. bornane-10,2-sultams, N-acylsultams, and (camphorsulfonyl)oxaziridines in asym. synthesis of amino acids, aldol condensations, and asym. alkylations with 14 references

Chimica Oggi published new progress about Chiral synthons. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Category: isothiazole.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Bunnage, Mark E.; Burke, Anthony J.; Davies, Stephen G.; Goodwin, Christopher J. published the artcile< Asymmetric synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid: the unknown amino acid component of microginin>, Application In Synthesis of 104322-63-6, the main research area is asym synthesis aminohydroxydecanoic acid; absolute configuration microginin aminohydroxydecanoic acid.

3-Amino-2-hydroxydecanoic acid (AHDA) is an unusual amino acid purported to occur in the recently isolated angiotensin-converting enzyme inhibitor microginin. In order to elucidate the stereochem. of the naturally occurring material, and thus complete the structural assignment of microginin, both the (2R,3R)-anti-diastereoisomer and the (2S,3R)-syn-diastereoisomer of AHDA have been prepared Comparison of the 1H and 13C NMR spectroscopic data of the synthetic amino acids with that reported for the naturally occurring material indicates that the relative stereochem. of the AHDA found in microginin is syn. The absolute stereochem. of the natural amino acid is shown to be (2S,3R) by comparison of its reported CD spectrum with that recorded for the synthetic material prepared herein.

Tetrahedron: Asymmetry published new progress about Absolute configuration. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Application In Synthesis of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Josien, Hubert; Curran, Dennis P. published the artcile< Synthesis of (S)-mappicine and mappicine ketone via radical cascade reaction of isonitriles>, 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 mappicine synthesis; radical cascade isonitrile.

(S)-mappicine (I) and mappicine ketone were prepared from Me acetoacetate by a strategy featuring a radical cascade reaction of II with Ph isonitrile as the key step. The introduction of the hydroxy group of (S)-mappicine occurred with moderate selectivity through asym. hydroxylation.

Tetrahedron published new progress about Radical cyclization. 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

Davis, Franklin A.; Weismiller, Michael C. published the artcile< Enantioselective synthesis of tertiary α-hydroxy carbonyl compounds using [(8,8-dichlorocamphoryl)sulfonyl]oxaziridine>, Formula: C10H15NO3S, the main research area is carbonyl compound alpha hydroxy asym synthesis; chlorocamphorylsulfonyloxaziridine oxidizing agent; tetralone enolate oxidation asym oxaziridine.

Very high stereoinduction, generally 90-95% ee, is observed for the asym. oxidation of 2-substituted-1-tetralone enolates to 2-hydroxy-2-substituted-1-tetralones by (+)-(8,8-dichlorocamphorylsulfonyl)oxaziridine (I), a new oxaziridine type. Not only are these tertiary-α-hydroxy carbonyl compounds difficult to prepare, enantiomerically pure, via other methods, but they are also models for several biol. active compounds This new asym. oxidizing reagent also affords exceptional ee’s for the asym. oxidation of acyclic ketone enolates as well. For example, oxidation of the sodium enolate of 1-phenylpropanone with I affords (S)-2-hydroxy-1-phenylpropanone in greater than 95% ee. I is prepared in two steps, in good overall yield, from (camphorsulfonyl)imine II. The results of this study demonstrate that modification of the oxaziridine active site is an efficient method for improving enolate oxidation stereoselectivities.

Journal of Organic Chemistry published new progress about Oxidation, stereoselective. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Formula: C10H15NO3S.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Fujiwara, Kenshu; Goto, Akiyoshi; Sato, Daisuke; Kawai, Hidetoshi; Suzuki, Takanori published the artcile< Stereoselective synthesis of cis- and trans-2,3-disubstituted eight-membered medium-ring ethers based on Ireland-Claisen rearrangement of 3-alkoxy-2-propenyl glycolate esters and ring-closing olefin metathesis>, Reference of 104322-63-6, the main research area is alkoxy propenyl glycolate ester preparation Ireland Claisen rearrangement; ether preparation ring closing olefin metathesis; disubstituted eight membered medium ring ether stereoselective preparation.

A simple stereoselective synthesis of cis- and trans-2,3-disubstituted medium-sized cyclic ethers was developed based on geometry-selective synthesis of 3-alkoxy-2-propenyl glycolate esters, Ireland-Claisen rearrangement of the glycolate esters, and ring-closing olefin metathesis.

Tetrahedron Letters published new progress about Cyclization (olefin metathesis). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Reference 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

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

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

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