Tag: M.W=200-250

Bunnage, Mark E.; Davies, Stephen G.; Goodwin, Christopher J. published the artcile< Asymmetric synthesis of homochiral syn- and anti-3-phenylisoserine derivatives: a practical strategy for the synthesis of the taxol C-13 side chain>, Reference of 104322-63-6, the main research area is taxol side chain asym synthesis; phenyisoserine homochiral derivative; cinnamate conjugate addition lithium methylbenzylbenzylamide; oxaziridine hydroxylation taxol sidechain precursor.

A tandem lithium amide conjugate addition-electrophilic hydroxylation approach to the synthesis of N-benzoyl-3-phenylisoserine Me esters affords a strategy for the practical synthesis of the taxol side chain. Thus, conjugate addition of (R)-PhCHMeN(Li)CH2Ph to (E)-PhCH:CHCO2CMe3 followed by hydroxylation with oxaziridine I gave 86% ester II (95% diastereomeric excess).

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about Hydroxylation. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Reference of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Davis, Franklin A.; Sheppard, Aurelia C. published the artcile< Oxidation of enamines to α-hydroxy ketones and α-amino ketones using N-sulfonyloxaziridines>, 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 enamine oxidation sulfonyloxaziridine; ketone hydroxy amino.

Tri-substituted enamines are oxidized to α-hydroxy ketones by N-sulfonyloxaziridines while di-substituted enamines are oxidized to α-amino ketones. A unified mechanism for the formation of both α-hydroxy ketones and α-amino ketones is proposed.

Tetrahedron Letters published new progress about Amines, keto 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

Bunnage, Mark E.; Burke, Anthony J.; Davies, Stephen G.; Goodwin, Christopher J. published the artcile< Asymmetric synthesis of the N-terminal component of microginin: (2S,3R)-3-amino-2-hydroxydecanoic acid, its (2R,3R)-epimer and (3R)-3-aminodecanoic acid>, Category: isothiazole, the main research area is asym synthesis microginin aminohydroxydecanoic acid; absolute configuration microginin aminohydroxydecanoic acid.

3-Amino-2-hydroxydecanoic acid (AHDA) is a novel amino acid which has been suggested as the N-terminal component of the recently isolated angiotensin-converting enzyme inhibitor microginin. The naturally occurring amino acid was found to possess syn relative stereochem. and (2S,3R) absolute stereochem. when the reported 1H and 13C NMR spectroscopic data and the CD data were compared to the spectroscopic data for synthetic (2R,3R)- and (2S,3R)-AHDA. These studies complete the stereochem. assignment of microginin.

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

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Bunnage, Mark E.; Davies, Stephen G.; Goodwin, Christopher J.; Ichihara, Osamu published the artcile< An expeditious asymmetric synthesis of allophenylnorstatine>, Formula: C10H15NO3S, the main research area is asym synthesis allophenylnorstatine; norstatine allophenyl asym synthesis.

The title compound, (2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid, a novel amino acid found in the kynostatin class of HIV-1 protease inhibitors, was prepared in 39% overall yield via a tandem conjugate addition-electrophilic hydroxylation protocol using lithium (S)-(α-methylbenzyl)benzylamide and (+)-(camphorsulfonyl)oxaziridine. An unprecedented level of mol. recognition between a homochiral β-amino enolate and a homochiral oxaziridine is identified and the importance of enolate geometry upon hydroxylation stereoselectivity is also addressed.

Tetrahedron published new progress about Stereoselective synthesis. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Formula: 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>, Application In Synthesis of 104322-63-6, 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, Application In Synthesis of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Page, Philip C. Bulman; Heer, Jag P.; Bethell, Donald; Lund, Andrew; Collington, Eric W.; Andrews, David M. published the artcile< A convenient procedure for the preparation of camphorsulfonyl oxaziridines>, Application of C10H15NO3S, the main research area is camphorsulfonyl oxaziridine preparation.

The title oxaziridines I (X,X = H, OCH2CH2O, OMe, OEt, Cl) were prepared by H2O2 oxidation of the imines II.

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

Wada, Takeshi; Mochizuki, Akira; Sato, Yuichi; Sekine, Mitsuo published the artcile< A convenient method for phosphorylation involving a facile oxidation of H-phosphonate monoesters via bis(trimethylsilyl)phosphites>, HPLC of Formula: 104322-63-6, the main research area is alc phosphonylation sulfonyloxaziridine nucleotide preparation; methylsilylbenzamide camphorsulfonyloxaziridine silylation nucleotide phosphonate; nucleoside phosphorylation oxidation silyl phosphite preparation.

A new convenient route to phosphate monoesters from alcs. has been developed. H-Phosphonate monoesters, which are readily accessible by phosphonylation of the parent alcs., were oxidized with t-BuOOH or N-sulfonyloxaziridines under anhydrous conditions via the corresponding bis(trimethylsilyl) phosphites. N,O-Bis(trimethylsilyl)benzamide (BSB) and (camphor-sulfonyl)oxaziridine (CSO) were found to be highly effective for silylation of H-phosphonates and oxidation of silyl phosphites, resp.

Tetrahedron Letters published new progress about Nucleotides Role: SPN (Synthetic Preparation), 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

Bunnage, Mark E.; Chernega, Alexander N.; Davies, Stephen G.; Goodwin, Christopher J. published the artcile< Asymmetric synthesis of β-amino-α-hydroxy acids via diastereoselective hydroxylation of homochiral β-amino enolates>, Formula: C10H15NO3S, the main research area is amino hydroxy acid stereoselective preparation; alkenoate conjugate addition amine; enolate amino preparation stereoselective hydroxylation.

The highly diastereoselective conjugate addition of lithium N-benzyl-N-α-methylbenzylamide with enoate acceptors, and the electrophilic hydroxylation of the resultant β-amino enolates with (camphorsulfonyl)oxaziridine, is identified as a direct and general strategy for the asym. synthesis of homochiral β-amino-α-hydroxy acids and their derivatives A structurally diverse array of β-amino enolate substrates can be hydroxylated with generally excellent anti diastereoselectivity (>90% d.e.) using this protocol; an alternative stepwise hydroxylation procedure, where the β-amino enolate is prepared by enolization of the preformed conjugate adduct also led to the anti diastereoisomer. The diastereofacial selectivity of enolate hydroxylation appears to be under predominantly substrate-controlled asym. induction, although a measurable degree of chirality recognition with the oxaziridine reagent can be observed Homochiral β-amino-α-keto esters are also prepared and their stereoselective reductions examined

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) 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, Formula: C10H15NO3S.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Davis, Franklin A.; Kumar, Anil; Reddy, Rajarathnam E.; Chen, Bang Chi; Wade, Peter A.; Shah, Sharmila W. published the artcile< Hydroxylation of dihydroisoxazoles using N-sulfonyloxaziridines>, Electric Literature of 104322-63-6, the main research area is hydroxylation dihydroisoxazole sulfonyloxaziridine; isoxazole dihydro hydroxylation; stereoselective hydroxylation dihydroisoxazole; oxaziridine sulfonyl hydroxylation.

Enantiomerically enriched 4-isoxazolols I (R = Ph, PhS, PhSO2, PhO, R1 = H; R = Ph, R1 = Bu) (26-71% ee) with predictable absolute configuration are available in good yield by hydroxylation of the aza-enolates of 4,5-dihydroisoxazoles (DHI’s) II with (camphorsulfonyl)oxaziridines III (X = H, Cl, MeO). This method is recommended over other oxidation procedures for the preparation of I because of its efficiency, ability to produce chiral products and the avoidance of toxic HMPA.

Journal of Organic Chemistry published new progress about Hydroxylation, 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

Cermak, Diana M.; Du, Yanming; Wiemer, David F. published the artcile< Synthesis of Nonracemic Dimethyl α-(Hydroxyfarnesyl)phosphonates via Oxidation of Dimethyl Farnesylphosphonate with (Camphorsulfonyl)oxaziridines>, Category: isothiazole, the main research area is hydroxyfarnesylphosphonate preparation oxidation camphorsulfonyloxaziridine stereoselective.

Several strategies for synthesis of nonracemic di-Me α-(hydroxyfarnesyl)phosphonate and the parent phosphonic acid have been explored. Separation of diastereomeric derivatives prepared by esterification of racemic α-hydroxy phosphonate with (S)-(+)-O-methylmandelic acid was possible, and these diastereomers could be assigned absolute stereochem. on the basis of literature precedent. However, hydrolysis to the α-hydroxy phosphonic acid was accompanied by extensive isomerization. Addition of a nonracemic phosphonamidite to farnesal also gave nonracemic material, but again hydrolysis was problematic. Oxidation of di-Me farnesylphosphonate anion with nonracemic (camphorsulfonyl)oxaziridines was shown to be regio- and stereoselective for formation of the α-hydroxy phosphonate. Enantiomeric excess of ∼70% ee was established by conversion of the oxidation products to their (S)-(+)-O-methylmandelate derivatives Although hydrolysis of these Me esters was accompanied by extensive racemization, both enantiomers of α-(hydroxyfarnesyl)phosphonic acid were obtained in low ee by this strategy.

Journal of Organic Chemistry published new progress about Selective oxidation (regio- and stereoselective). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Category: isothiazole.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com