Category: isothiazole

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

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

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

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

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 Letters published 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

Towson, James C.; Weismiller, Michael C.; Lal, G. Sankar; Sheppard, Aurelia C.; Kumar, Anil; Davis, Franklin A. published the artcile< Synthesis of (+)-(2R,8aS)-10-(camphorylsulfonyl)oxaziridine>, SDS of cas: 104322-63-6, the main research area is camphorylsulfonyloxaziridine; oxaziridine camphorylsulfonyl.

Amidation of (+)-10-camphosulfonyl chloride by NH4OH in CH2Cl2 gave 90% (+)-(1S)-1-camphorsulfonamide which underwent Amberlyst 15 catalyzed cyclocondensation in PhMe to give 90-95% imine I. The last was treated with aqueous oxone and K2CO3 to give 84% title compound II.

Organic Syntheses published new progress about 104322-63-6. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, SDS of cas: 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

McClure, Cynthia K.; Grote, Christopher W. published the artcile< α,β-Functionalization of enones via pentacovalent oxaphospholenes>, Application In Synthesis of 104322-63-6, the main research area is oxaphospholene functionalization enone; phosphonate keto acylvinyl.

2,2,2-Triethoxy-1,2λ5-oxaphospholene reacts under mild, neutral conditions with bromine, dialkyl azodicarboxylates, and oxaziridines to produce β-heteroatom substituted γ-ketophosphonates and β-acyl vinyl phosphonate in high yields.

Tetrahedron Letters published new progress about 104322-63-6. 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

Bunnage, Mark E.; Davies, Stephen G.; Goodwin, Christopher J. published the artcile< Asymmetric synthesis of allophenylnorstatine>, Application In Synthesis of 104322-63-6, the main research area is asym synthesis allophenylnorstatine; norstatine allophenyl asym synthesis.

The title compound (I), a component of the HIV-1 protease inhibitor kynostatin, has been prepared via a tandem conjugate addition-electrophilic hydroxylation strategy using lithium (S)-(α-methylbenzyl)benzylamide and (+)-(camphorsulfonyl)oxaziridine. The effects of mol. recognition and enolate geometry on the selectivity of the reaction are discussed.

Synlett published new progress about Stereoselective synthesis. 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

Davis, Franklin A.; Lal, G. Sankar; Wei, Jia published the artcile< Stereo- and regioselective formation of silyl enol ethers via oxidation of vinyl anions>, Application In Synthesis 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, Application In Synthesis 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>, Synthetic Route of 104322-63-6, 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, Synthetic Route of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com