79749-96-5

Upstream product

• 5739-83-3 methyl trans-4-hydroxy-4-methyl-2-pentenoate 
• 108-98-5 thiophenol 
• 63996-66-7 2-methyl-2-(phenylthio)propanal 
• 5042-53-5 1-(phenylsulfanyl)acetone 
• 499776-31-7 3-hydroxy-4-phenylsulfanyl-4-methylpentanenitrile 
• 910865-12-2 3-hydroxy-4-methyl-4-phenylsulfanyl-pentanamide 
• 910865-31-5 4-(3'-hydroxy-4'-methyl-4'-phenylsulfanyl-pentanoylamino)-4-methyl-pentanoic acid 
• 910865-30-4 methyl 4-(3'-hydroxy-4'-methyl-4'-phenylsulfanyl-pentanoylamino)-4-methyl-pentanoate 
• 910865-29-1 tert-butyl-4-(3'-hydroxy-4'-methyl-4'-phenylsulfanyl-pentanoylamino)-4-methyl-pentanoate 
• 910865-10-0 3-hydroxy-4-methyl-4-(phenylthio)pentanoic acid 
• 910865-11-1 ethyl 3-hydroxy-4-methyl-4-(phenylthio)pentanoate 
• 910865-14-4 5,5-dimethyl-4-phenylsulfanyl-dihydro-furan-2-imine 
• 910865-37-1 N-(1'-carbamoyl-1'-methyl-ethyl)-3-hydroxy-4-methyl-4-phenylsulfanyl-pentanamide 
• 910865-32-6 3-hydroxy-4-methyl-4-phenylsulfanyl-(3'-carbomyl-1',1'-dimethyl-propyl)-pentanamide 

Downstream Products

• 882-33-7 diphenyldisulfane 
• 344305-99-3 4-Benzenesulfonyl-5,5-dimethyl-dihydro-furan-2-one 
• 84477-38-3 4-Benzenesulfinyl-5,5-dimethyl-dihydro-furan-2-one 
• 77199-32-7 4,4-dimethyl-3-(phenylthio)-2-buten-4-olide 

Relevant academic research and scientific papers

Episulfonium ion-mediated cyclic peptide and triazine synthesis

The product of an episulfonium ion-mediated cyclotrimerisation, previously reported as being a 15-membered ring trilactam, has now been shown to be a 1,3,5-triazine. Smaller medium-ring bilactams have, however, been synthesised from linear precursors usin

Sulfur mediated ritter reactions: The synthesis of cyclic amides

Simple β-hydroxy-γ-phenylsulfanyl nitriles undergo a selective Ritter reaction, onto a thiiranium (episulfonium) ion, to yield 15-membered triamides. This selective trimerisation allows the rapid synthesis of these macrocylic triamides.

Cyclization of 4-Hydroxy-(E)-2-alkenoic Esters: Simple Synthesis of Butenolides

Simple treatment of 4-hydroxy-(E)-2-alkenoic esters with benzenethiol leads to cyclization to give 3-phenylthio-4-alkanolides, which are easily converted into 3-phenylthio-2-alken-4-olides and 2-alken-4-olides (Δα,β-butenolides).

SELECTIVE REACTIONS OF THIOLATE ANIONS WITH 4-HYDROXY-E-2-ALKENOIC ESTERS OR 4-METHANESULFONYLOXY-E-2-ALKENOIC ESTERS. SYNTHESIS OF 2-ALKEN-4-OLIDES (Δα,β-BUTENOLIDES) AND E,E-2,4-ALKADIENOIC ESTERS

Methyl 4-hydroxy-E-2-alkenoates prepared from aldehydes in one step, undergo the Michael reactions with thiolate anions to give 4-alkanolide derivatives, which are converted into 2-alken-4-olides.Methyl 4-methanesulfonyloxy-E-2-alkenoates undergo the substitution reactions, and subsequent treatments give methyl E,E-2,4-alkadienoates.

Synthesis of Butenolides from α-(Phenylthio)-ketones and -esters: Crystal Structure of an Intermediate β-Phenylthio-γ-lactone

Alkylation of α-(phenylthio)-ketones or -esters with iodoacetate anion gives 1,4-dicarbonyl compounds which are reduced stereoselectively to β-phenylthio-γ-butyrolactones.Oxidation to sulphoxides and thermolysis provides a general synthesis of β- and γ-substituted Δαβ-butenolides.Treatment of 5,5-dimethyl-4-oxo-3-(phenylthio)-hexanoic acid with NaBH4 gives a single γ-lactone whose PhS and But groups are shown to be cis by X-ray crystal structure determination.