16166-53-3

Upstream product

• 286-20-4 cyclohexane-1,2-epoxide 
• 3385-94-2 hexamethyldisilathiane 
• 108-94-1 cyclohexanone 
• 22551-20-8 (+/-)-cis-1-acetoxy-2-acetylsulfanyl-cyclohexane 
• 1424-22-2 1-cyclohexenyl acetate 
• 286-20-4 cyclohexene oxide 

Downstream Products

• 22551-20-8 (+/-)-trans-1-acetoxy-2-acetylsulfanyl-cyclohexane 
• 58198-41-7 trans-2-ethylsulfanyl-cyclohexanol 
• 27040-92-2 Bis-(2-hydroxy-cyclohexyl)-disulfid 
• 16767-94-5 <2-Hydroxy-cyclohexyl>-<2-mercaptocyclohexyl>-sulfid 
• 286-28-2 7-thiabicyclo[4.1.0]heptane 
• 286-28-2 cyclohexene sulfide 

Relevant academic research and scientific papers

Regio- and stereoselective ring-opening of epoxides using organic dithiophosphorus acids as nucleophiles

A practical method for the synthesis of β-hydroxymercaptans has been successfully developed through the ring-opening of epoxides with organic dithiophosphorus acids 1. Highly regio- and stereoselective products, β-hydroxyalkyl dithiophosphates, which were transformed to the corresponding synthetically valuable β-hydroxymercaptans by further reduction, were obtained under mild reaction conditions without any catalyst or promoter. Highly enantioselective ring-opening reaction of cyclohexene epoxide with 1 was realized in the presence of a chiral (salen)Ti(IV) complex.

Regio- and stereospecific synthesis of (O-tips)-protected 2- hydroxyalkylmercaptans from epoxides and triisopropylsilanethiol

The regiospecific ring-opening of both mono- and disubstituted epoxides with triisopropylsilanethiol/DBU has been developed to provide 2- triisopropylsilylaxyalkylthiols (1) in high yields. Non-racemic 1 is easily prepared from optically active epoxides. Moreover, the further elaboration of 1, through the exposed mercapto functionality, provides controlled access to unsymmetrical mono-protected bis-(2-hydroxyalkyl) sulfides and functionalized thioesters.

The efficient conversion of H2S into mercaptan alcohols mediated in protic ionic liquids under mild conditions

The resource utilization of hydrogen sulfide (H2S) is an important and promising topic in energy chemical engineering. Previous products developed in our group through H2S conversion are sulfur or mercaptan acids. An alternative way to convert H2S is still desirable. Herein, we have developed a green and mild method to convert H2S into mercaptan alcohols by the addition reaction with epoxide mediated in tertiary amine-functionalized protic ionic liquids (PILs). Reaction kinetics, substrate scope, and regeneration experiments have all been explored. Almost quantitative conversion of substrates was realized with a catalytic loading of PILs at 30 °C. Water extraction was used to recycle the catalysts from the reaction system. It is believed that the excellent results, together with its operational simplicity and the ability to successively reuse the catalyst, make this new methodology environmentally benign and cost-effective. The generality of the H2S resource methodology gives it potential for application on an industrial scale.

PEPTIDE CONJUGATES OF CYTOTOXINS AS THERAPEUTICS

The present invention relates to peptide conjugates of cytotoxins such as topoisomerase I inhibitors which are useful for the treatment of diseases such as cancer.

TBD-catalyzed α-sulfenylation of cyclic ketones: Desymmetrization of 4-substituted cyclohexanones

A low loading of triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzes the α-sulfenylation reaction of ketones employing tetramethylthiuram disulfide (TMTDS) as electrophilic reagent. This methodology is mild, effective and straightforward, rendering the desired products in high yield. Prochiral 4-substituted cyclohexanones can be desymmetrized with remarkable diastereoselectivity following this protocol. The dithiocarbamoyl function was shown to be easily removed upon reduction, affording thiols (1-mercaptan-2-ols).

Regio- and enantioselective ring-opening of epoxides with HMDST: A straightforward access to 1,2-mercaptoalcohols

TBAF-catalyzed reaction of a range of substituted epoxides with hexamethyldisilathiane smoothly affords a direct and simple access to β-mercaptoalcohols in a highly regio- and stereo-selective way. Georg Thieme Verlag Stuttgart.

The cleavage of meso-epoxides with homochiral thiols: Synthesis of (+)- and (-)-trans-1-mercaptocyclohexan-2-ol

The synthesis of (+)- and (-)-trans-1-mercaptocyclohexan-2-ol is described. Ring opening of cyclohexene oxide with (-)-4-methoxybenzylnopan- 3(R)-thiol 1a followed by oxidation gives two readily separable diastereomeric sulfoxides. These sulfoxides display very different thermal stability but both undergo regio-specific syn-elimination to give cyclohexan- 1-ol-2-sulfenic acid that can be reacted in situ with 3,5-dimethylthiophenol to give a mixed disulfide. Reduction of these disulfides with lithium aluminium hydride gives the title compounds in enantiomerically pure form.

Direct synthesis of thiols from halides and epoxides using hydrosulfide exchange resin in methanol

Various thiols are prepared directly from the corresponding alkyl halides and epoxides using hydrosulfide exchange resin in methanol in the presence of equimolar amounts of triethylammonium chloride at room temperature. The reaction not only proceeds with unique chemoselectivity, but also gives better yields of thiols than most commonly used indirect methods and has an additional advantage of a simple workup.

Triphenylsilanethiol: A solid H2S equivalent in the ring opening of epoxides

Triphenylsilanethiol, a white crystalline solid, can be used in the opening of epoxides to form β-hydroxymercaptans or β-dihydroxysulfides.

THE CHEMISTRY OF α,ω-MERCAPTOALCOHOLS IN THE PRESENCE OF DIETHOXYTRIPHENYLPHOSPHORANE. TEMEPERATURE DEPENDENCE OF CYCLODEHYDRATIONS AND S-ETHYLATIONS

Diethoxytriphenylphosphorane (DTPP) is easily prepared by oxidative addition of triphenylphosphine with diethyl peroxide.DTPP converts a variety of mercaptoalcohols to cyclic sulfides as well as hydroxythioethers.The temperature dependence (+25 --> -25 deg C) of the product distribution has synthetic petential.