Urea-hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
Adesh Kumar Singh1, Varsha Tiwari1, Kunj Bihari Mishra1
1Department of Chemistry, Indian Institute of Technology, Banaras Hindu University, Varanasi-221005, India.
Abstract:
A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea-hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin functional groups were found to be stable during the oxidation of sulfide.
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