4973-66-4

Usage

InChI:InChI=1/C8H10O2S2/c1-7-3-5-8(6-4-7)12(9,10)11-2/h3-6H,1-2H3

Upstream product

• 68305-24-8 S-methyl p-toluenethiosulfinate 
• 5813-48-9 Methanesulfenyl chloride 
• 28519-50-8 potassium thiotosylate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 74-88-4 methyl iodide 
• 3753-27-3 sodium 4-methylbenzenesulfonothioate 
• 20277-69-4 sodium methansulfinate 
• 271574-43-7 α-tosyl dimethyldisulfide 
• 42474-28-2 α-mesyl dimethyldisulfide 
• 59534-02-0 chloro-phenylsulfanyl-(toluene-4-sulfonyl)-methanesulfenyl chloride 
• 624-92-0 Dimethyldisulphide 
• 77-78-1 dimethyl sulfate 
• 110-91-8 morpholine 
• 72087-89-9 C₁₆H₁₅ClO₃S₄ 

Downstream Products

• 856343-92-5 1-methylsulfanyl-1-(toluene-4-sulfonyl)-acetone 
• 23566-08-7 benzenesulfonyl-bis-methanesulfonyl-methane 
• 899-02-5 (2,4-dinitro-phenyl)-p-tolyl sulfone 
• 60416-89-9 (4-chloro-benzenesulfonyl)-methylsulfanyl-methane 
• 856060-70-3 ethanesulfonyl-benzenesulfonyl-methylsulfanyl-methane 
• 856165-03-2 benzenesulfonyl-methylsulfanyl-(toluene-4-sulfonyl)-methane 
• 21127-78-6 Benzylmethansulphenat 
• 14758-37-3 2-methylthio-1,3-dithiane 
• 18306-29-1 bis(trimethylsilyl)sulphate 
• 70801-53-5 2-methylsulfanyl-3-oxo-3-phenyl-propionitrile 
• 100-03-8 4-chlorobenzenesulfinic acid 
• 59662-65-6 methylthiomethyl p-tolyl sulfone 
• 3795-79-7 methyl 4-(methylthio)benzoate 
• 1152443-07-6 ethyl 6,7-dihydro-7,7-dimethyl-5-oxo-1-phenyl-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylate 

Relevant academic research and scientific papers

Synthesis and Molecular Properties of Partially Fluorinated DNTTs**

1,2,3,4-Tetrafluoro-dinaphthothienothiophene (F4DNTT) and 1,2,3,4,8,9,10,11-octafluoro-dinaphthothienothiophene (F8DNTT) were synthesized via bisthiomethyl alkene intermediates which were accessible by McMurry coupling or Wittig olefination of partially fluorinated naphthalene precursors. DFT-based electronic structure calculations, near-edge X-ray absorption fine structure (NEXAFS) spectroscopy, and UV/Vis measurements were used for HOMO/LUMO gap determination and to analyze the electronic structures of the partially fluorinated DNTTs. Reduced exciton binding was observed in thin films.

Enantioselective Copper-Catalyzed Electrophilic Sulfenylation of Cyclic Imino Esters

Herein we report an enantioselective sulfenylation of cyclic imino esters with the efficient and versatile sulfenylation reagent S-alkyl 4-methylbenzenesulfonothioates. By utilizing the Cu/tBu-Phosferrox catalytic system, we can assemble diverse S-alkyl groups into the cyclic imino esters under mild conditions in good yields and with excellent enantioselectivities. Remarkably, this method demonstrates a high tolerance of diverse functional groups and proves to be applicable in the late-stage functionalization of pharmaceuticals.

Rh(ii)/phosphine-cocatalyzed synthesis of dithioketal derivatives from diazo compounds through simultaneous construction of two different C-S bonds

Rhodium(ii)/phosphine-cocatalyzed bis-sulfuration of α-diazocarbonyl compounds using thiosulfonates as the sulfenylating agent, which provided two sulfur-containing moieties, was developed via simultaneous inter- and intra-molecular C-S bond formation. This novel protocol provides a rapid synthetic route to dithioketal derivatives in moderate to good yields in an atom-economic process. The transformation is proposed to proceed through phosphine ylide formation followed by S(O2)-S bond cleavage and rearrangement.

Formal Total Synthesis of (+)-C9-Deoxyomuralide from l -Leucine Using a Double Sacrificial Chirality Transfer Approach

Formal stereocontrolled syntheses of (±)- and (+)-C9-deoxyomuralide is reported, constituting one of the shortest routes to the full carbon skeleton reported to date.

Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles

Non-oxidative, regioselective, and convergent access to densely functionalized oxazoles is realized in a functional-group tolerant manner using alkynyl thioethers. Sulfur-terminated alkynes provide access to reactivity previously requiring strong donor-substituted alkynes such as ynamides. Sulfur does not act in an analogous donor fashion in this gold-catalyzed reaction, thus leading to complementary regioselective outcomes and addressing the limitations of using ynamides.

Substituted pyridine and pyrimidine derivatives and their use in treating viral infections

The present invention provides compounds of Formula (I): and tautomers, isomers, and esters of said compounds, and pharmaceutically acceptable salts, solvates, and prodrugs of said compounds, wherein each of R, R1, X, Y, Z, R2, R3, R4, R5, R6, R7, R8, R9, R18, R19 and n is selected independently and as defined herein. Compositions comprising such compounds are also provided. The compounds of the invention are effective as inhibitors of HCV, and are useful, alone and together with other therapeutic agents, in treating or preventing diseases or disorders such as viral infections and virus-related disorders.

Oxidative coupling of dichalcogenides with sodium sulfinates via copper-catalyzed cleavage of s-s and se-se bonds

A copper-catalyzed sulfonylation of disulfides was achieved using sodium sulfinates in air. The reaction formed various sulfur-sulfone bonds efficiently and afforded thiosulfonates in good yields. Selenosulfonates could also be prepared with this procedure. Furthermore, both chalcogenide groups on the dichalcogenides were available in these reactions.

A mild and facile synthesis of aryl and alkenyl sulfides via copper-catalyzed deborylthiolation of organoborons with thiosulfonates

An efficient deborylthiolation of aryl- and alkenylborons with thiosulfonates has been achieved under mild conditions using a copper catalyst. All steps of the experimental process were free from unpleasant odors. The mild reaction conditions as well as ready availability of boron compounds and thiosulfonates enabled easy access to an array of sulfides, including those bearing sensitive functional groups.

NBS-promoted sulfenylation of sulfinates with disulfides leading to unsymmetrical or symmetrical thiosulfonates

A highly practical method to access unsymmetrical and symmetrical thiosulfonates in moderate to excellent yields has been developed through NBS-promoted sulfenylation of sulfinates with disulfides. The present process enables the use of two RS in RSSR and shows broad functional group tolerance, which represents an atom-economical and practical procedure for the synthesis of thiosulfonates. A plausible mechanism for the role of NBS as a promoter for the cleavage of disulfides generating N-(organothio)succinimide that then undergos facile sulenylation with sulfinates is proposed. Copyright

Structure-activity studies on the anti-proliferation activity of ajoene analogues in WHCO1 oesophageal cancer cells

The organosulfur compound ajoene derived from the rearrangement of allicin found in crushed garlic can inhibit the proliferation of tumour cells by inducing G2/M cell cycle arrest and apoptosis. We report on the application of a concise four-step synthesis (Hunter et al., 2008 [1]) that allows access to ajoene analogues with the end allyl groups substituted. A library of twelve such derivatives tested for their anti-proliferation activity against WHCO1 oesophageal cancer cells has identified a derivative containing p-methoxybenzyl (PMB)-substituted end groups that is twelve times more active than Z-ajoene, with an IC50 of 2.1 μM (Kaschula et al., 2011 [2]). Structure-activity studies involving modification of the sulfoxide and vinyl disulfide groups of this lead have revealed that the disulfide is the ajoene pharmacophore responsible for inhibiting WHCO1 cell growth, inducing G 2/M cell cycle arrest and apoptosis by caspase-3 activation, and that the vinyl group serves to enhance the anti-proliferation activity a further eightfold. Reaction of the lead with cysteine in refluxing THF as a model reaction for ajoene's mechanism of action based on a thiol/disulfide exchange reveals that the allylic sulfur of the vinyl disulfide is the site of thiol attack in the exchange.