5056-07-5

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-METHYL P-TOLYL SULFOXIDE is used as a nucleophilic reagent for the synthesis of optically active β-disulfoxides. This application is crucial for the development of enantiomerically pure compounds, which are essential in the pharmaceutical industry for the production of chiral drugs with specific biological activities.
Used in Organic Synthesis:
(S)-(-)-METHYL P-TOLYL SULFOXIDE is used as a nucleophilic reagent for the preparation of α-substituted N-hydroxylamines by treating with nitrones. This reaction is important in organic synthesis, as N-hydroxylamines are versatile intermediates for the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds.
Used in Carbohydrate Chemistry:
(S)-(-)-METHYL P-TOLYL SULFOXIDE is used as a nucleophilic reagent for the one-carbon homologation of 2,3-O-isopropylidene-L-glyceraldehyde to produce 2-O-benzyl-3,4-O-isopropylidene-L-erythrose. This reaction is significant in carbohydrate chemistry, as it allows for the synthesis of modified carbohydrates with potential applications in the development of new drugs, vaccines, and other bioactive compounds.

InChI:InChI=1/C8H10OS/c1-7-3-5-8(6-4-7)10(2)9/h3-6H,1-2H3/t10-/m1/s1

Upstream product

• 917-64-6 methyl magnesium iodide 
• 52154-24-2 (R)-p-tolylsulfinylacetophenone 
• 623-13-2 4-methylphenyl methylsulfide 
• 75-16-1 methylmagnesium bromide 
• 142635-30-1 (4S)-4-benzyl-3-<(S)-p-tolylsulfinyl>-2-isoxazolidinone 
• 31350-91-1 (R)-chloromethyl p-tolyl sulfoxide 
• 134311-28-7 (+)-(1S,2R)-trans-2-phenylcyclohexyl (S)-methanesulfinate 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 135802-77-6 (S_S)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl methanesulfinate 
• 934-72-5 Methyl p-tolyl sulfoxide 
• 114026-76-5 (-)-(2R,3R)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4.5]decane 
• 169330-85-2 (+)-(S)-N-propanoyl-N-benzyl-p-toluenesulfinamide 
• 158109-78-5 (R,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 170956-16-8 4-Methyl-benzenesulfinic acid 1-naphthalen-1-yl-meth-(E)-ylideneamide 

Downstream Products

• 142722-58-5 (S)-(-)-1-fluoro-3-<(4-methylphenyl)sulphinyl>propan-2-one 
• 113002-37-2 5-Methyl-1-((R)-toluene-4-sulfinyl)-hexan-2-one 
• 131617-81-7 (-)-(S)-5-Methyl-1-(p-tolylsulfinyl)-5-hexen-2-one 
• 121898-05-3 (S)-(-)-1-chloro-1,1-difluoro-3-<(4-methylphenyl)sulphinyl>propan-2-one 
• 133343-42-7 1-Chloro-1,1-difluoro-3-((S)-toluene-4-sulfinyl)-propane-2,2-diol 
• 132164-16-0 (2R,S_S)-(-)-1-chloro-1,1-difluoro-3-(p-tolylsulphinyl)propan-2-ol 
• 133343-49-4 (S)-1-Chloro-1,1-difluoro-3-((S)-toluene-4-sulfinyl)-propan-2-ol 
• 133343-44-9 1,1-Dichloro-1-fluoro-3-((S)-toluene-4-sulfinyl)-propane-2,2-diol 
• 132164-18-2 (2R,S_S)-1,1-Dichloro-1-fluoro-3-<(4-methylphenyl)sulfinyl>propan-2-ol 
• 133343-51-8 (S)-1,1-Dichloro-1-fluoro-3-((S)-toluene-4-sulfinyl)-propan-2-ol 
• 155671-28-6 (S)-3-(2-Methoxy-ethoxymethoxy)-1-((S)-toluene-4-sulfinyl)-butan-2-one 
• 90988-94-6 (4S,6S)-4-(2-Benzyloxy-ethyl)-2,2-dimethyl-6-[2-((S)-toluene-4-sulfinyl)-ethyl]-[1,3]dioxane 
• 155671-29-7 (S)-1-Methoxymethoxy-1-phenyl-3-((S)-toluene-4-sulfinyl)-propan-2-one 
• 24824-93-9 chloromethyl p-tolyl sulfoxide 

Relevant academic research and scientific papers

Diketobile acids as new hosts in solid-state enantioselective resolutions

New diketobile acid derivatives have been evaluated as hosts in the resolution of aryl methyl sulfoxides. The guest molecules are linked to the host ones via hydrogen bonds with the SO group. The 3,6-diketo derivative is also effective for the resolution of γ-lactames. Copyright

Discovery and application of methionine sulfoxide reductase B for preparation of (S)-sulfoxides through kinetic resolution

Here we report a methionine sulfoxide reductase B (MsrB) enzymatic system for the preparation of (S)-sulfoxides through kinetic resolution of racemic (rac) sulfoxides. Eight MsrB homologue recombinant proteins were expressed and their activities on asymmetric reduction of rac-sulfoxides were analyzed. Among these MsrB homologue proteins, one protein from Acidovorax species showed good activity and enantioselectivity towards several aryl-alkyl sulfoxides. The (S)-sulfoxides were prepared with 93–98% enantiomeric excess through kinetic resolution at initial substrate concentration up to 50 mM. The establishment of MsrB catalytic kinetic resolution system provides a new efficient green strategy for preparation of (S)-sulfoxides.

Chiral: N, N ′-dioxide-iron(iii)-catalyzed asymmetric sulfoxidation with hydrogen peroxide

A highly enantioselective sulfoxidation of various sulfides has been achieved by a N,N′-dioxide-iron(iii) complex with 35% aq. H2O2 as the oxidant. The utility of the current method was demonstrated by asymmetric gram-scale synthesis of drug molecule (R)-modafinil. Moreover, a possible working mode was provided to elucidate the chiral induction.

Highly Efficient Access to (S)-Sulfoxides Utilizing a Promiscuous Flavoprotein Monooxygenase in a Whole-Cell Biocatalyst Format

Chiral sulfoxides have gained attention as synthons and precursors for API synthesis. Flavoproteins such as Baeyer-Villiger or styrene monooxygenases mainly provide access to (R)-sulfoxides and often suffer from low selectivity, activity, and/or limited substrate scope. The flavoprotein monooxygenase AbIMO from Acinetobacter baylyi ADP1 initiates indole degradation. Here, AbIMO was expressed recombinantly in E. coli and characterized for its sulfoxidation activity and substrate spectrum. Next to indole and styrene, AbIMO was found to accept numerous alkyl aryl sulfides as substrates, transforming them to (S)-sulfoxides with high enantioselectivity (95 percent to '99 percent for most sulfides). The formulation as a whole-cell biocatalyst allowed specific production rates of up to 370 U gcdw?1 – the highest specific oxygenase activity achieved in whole cells so far – and the preparative synthesis of enantiopure (S)-aryl alkyl sulfoxides. With its extraordinarily high specific activity, high specificity, ease of handling, and high stability (catalyst is stable for '16 days at 4 °C), the designed whole-cell biocatalyst adds enormous value to the portfolio of chemical and biological catalysts for asymmetric sulfoxide synthesis.

Enzymatic kinetic resolution of chiral sulfoxides-an enantiocomplementary approach

A new enzymatic assay for the preparation of chiral sulfoxides that is enantiocomplementary to the known (S)-enantiomer-reducing activity of methionine sulfoxide reductase A (MsrA) is described. To this end, we have utilized the enzyme DMSO reductase (DmsABC), recently discovered by us being highly upregulated in stationary phase E. coli bacteria.

Molybdenum-catalyzed enantioselective sulfoxidation controlled by a nonclassical hydrogen bond between coordinated chiral imidazolium-based dicarboxylate and peroxido ligands

Chiral alkyl aryl sulfoxides were obtained by molybdenum-catalyzed oxidation of alkyl aryl sulfides with hydrogen peroxide as oxidant in mild conditions with high yields and moderate enantioselectivities. The asymmetry is generated by the use of imidazoli

Method for catalyzing asymmetric oxidation of sulfur ether

The invention provides a method for asymmetrically oxidizing sulfur ether. The sulfur ether is subjected to asymmetric catalytic oxidation reaction by taking a chiral complex formed by a four-tooth nitrogen organic ligand and a metal scandium compound as a catalyst and taking hydrogen peroxide as an oxidizing agent to obtain a corresponding chiral sulfoxide compound, and the yield and the enantioselectivity are more than 90 percent. The reaction has the advantages of cleanness, mild reaction condition, high conversion rate and high enantioselectivity. The method has an industrial prospect.

Ultrafast chiral separations for high throughput enantiopurity analysis

Recent developments in fast chromatographic enantioseparations now make high throughput analysis of enantiopurity on the order of a few seconds achievable. Nevertheless, routine chromatographic determinations of enantiopurity to support stereochemical investigations in pharmaceutical research and development, synthetic chemistry and bioanalysis are still typically performed on the 5-20 min timescale, with many practitioners believing that sub-minute enantioseparations are not representative of the molecules encountered in day to day research. In this study we develop ultrafast chromatographic enantioseparations for a variety of pharmaceutically-related drugs and intermediates, showing that sub-minute resolutions are now possible in the vast majority of cases by both supercritical fluid chromatography (SFC) and reversed phase liquid chromatography (RP-LC). Examples are provided illustrating how such methods can be routinely developed and used for ultrafast high throughput analysis to support enantioselective synthesis investigations.

Enantioselective Aromatic Sulfide Oxidation and Tandem Kinetic Resolution Using Aqueous H2O2 and Chiral Iron–Bis(oxazolinyl)bipyridine Catalysts

An efficient method for the oxidation of aromatic sulfides has been developed by using aqueous H2O2, catalyzed by the in situ generated chiral Fe/6,6′-bis(4-isopropyloxazolin-2-yl)-2,2′-bipyridine (bipybox-iPr) complex. The corresponding sulfoxides were obtained with high enantioselectivities (up to 98.5:1.5 er) and in good yields (up to 61 %) when the mono-oxidation of the sulfides was performed in combination with the kinetic resolution of the sulfoxide into the sulfone.

Peroxygenase-Catalyzed Enantioselective Sulfoxidations

The performances of the unspecific peroxigenase from Agrocybe aegerita (AaeUPO) in the asymmetric sulfoxidation of substituted aryl alkyl sulfides were here investigated. A small library of differently substituted aryl alkyl sulfoxides was successfully synthesized from the corresponding sulfides in the presence of AaeUPO and H2O2. All the sulfoxides were obtained as (R)-enantiomers, regardless the substitution pattern both on the aromatic ring and the alkyl chain, in up to > 99 % conversion and > 99 % ee. An overview about the biocatalytic entries to chiral sulfoxides is also presented here in form of a comparison between the results obtained with AaeUPO and performances of the chloroperoxidase from Caldariomyces fumago, and three different Baeyer–Villiger monooxygenases. To the best our knowledge, this is the first example of a systematic investigation of the AaeUPO synthetic potential in the asymmetric oxidation of hetero atoms, i.e., the pro-stereogenic sulfur of sulfides.