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Urea-hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones.

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.

SUBMITTER: Singh AK

PROVIDER: S-EPMC5480342 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Urea-hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones.

Singh Adesh Kumar AK Tiwari Varsha V Mishra Kunj Bihari KB Gupta Surabhi S Kandasamy Jeyakumar J

Beilstein journal of organic chemistry 20170613

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. ...[more]

PMID: 28684993

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