[HTML][HTML] Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

AK Singh, V Tiwari, KB Mishra, S Gupta… - Beilstein Journal of …, 2017 - beilstein-journals.org
Beilstein Journal of Organic Chemistry, 2017beilstein-journals.org
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.
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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