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

15 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.",

keywords = "Monosaccharides, Oxidation, Sulfones, Sulfoxides, Thioglycosides, Urea–hydrogen peroxide",

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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

Y1 - 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

UR - https://www.scopus.com/pages/publications/85020811130

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DO - 10.3762/bjoc.13.113

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AN - SCOPUS:85020811130

SN - 1860-5397

VL - 13

SP - 1139

EP - 1144

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

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

Abstract

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Keywords

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