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

Adesh Kumar Singh; Varsha Tiwari; Kunj Bihari Mishra; Surabhi Gupta; Jeyakumar Kandasamy

doi:10.3762/bjoc.13.113

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

Adesh Kumar Singh, Varsha Tiwari, Kunj Bihari Mishra, Surabhi Gupta, Jeyakumar Kandasamy

Indian Institute of Technology Banaras Hindu University

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

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.

Original language	English
Pages (from-to)	1139-1144
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	13
DOIs	https://doi.org/10.3762/bjoc.13.113
State	Published - 13 Jun 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 Singh et al.

Keywords

Monosaccharides
Oxidation
Sulfones
Sulfoxides
Thioglycosides
Urea–hydrogen peroxide

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10.3762/bjoc.13.113

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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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AU - Singh, Adesh Kumar

AU - Tiwari, Varsha

AU - Mishra, Kunj Bihari

AU - Gupta, Surabhi

AU - Kandasamy, Jeyakumar

PY - 2017/6/13

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AB - 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.

KW - Monosaccharides

KW - Oxidation

KW - Sulfones

KW - Sulfoxides

KW - Thioglycosides

KW - Urea–hydrogen peroxide

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JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

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

Abstract

Bibliographical note

Keywords

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