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

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...

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Detalles Bibliográficos
Autores principales: Singh, Adesh Kumar, Tiwari, Varsha, Mishra, Kunj Bihari, Gupta, Surabhi, Kandasamy, Jeyakumar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5480342/
https://www.ncbi.nlm.nih.gov/pubmed/28684993
http://dx.doi.org/10.3762/bjoc.13.113
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author Singh, Adesh Kumar
Tiwari, Varsha
Mishra, Kunj Bihari
Gupta, Surabhi
Kandasamy, Jeyakumar
author_facet Singh, Adesh Kumar
Tiwari, Varsha
Mishra, Kunj Bihari
Gupta, Surabhi
Kandasamy, Jeyakumar
author_sort Singh, Adesh Kumar
collection PubMed
description 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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spelling pubmed-54803422017-07-06 Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones Singh, Adesh Kumar Tiwari, Varsha Mishra, Kunj Bihari Gupta, Surabhi Kandasamy, Jeyakumar Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2017-06-13 /pmc/articles/PMC5480342/ /pubmed/28684993 http://dx.doi.org/10.3762/bjoc.13.113 Text en Copyright © 2017, Singh et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Singh, Adesh Kumar
Tiwari, Varsha
Mishra, Kunj Bihari
Gupta, Surabhi
Kandasamy, Jeyakumar
Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
title Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
title_full Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
title_fullStr Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
title_full_unstemmed Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
title_short Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
title_sort urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5480342/
https://www.ncbi.nlm.nih.gov/pubmed/28684993
http://dx.doi.org/10.3762/bjoc.13.113
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