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Article
Regenerative Glycosylation
The Journal of Organic Chemistry (2017)
  • Alexei Demchenko, University of Missouri-St. Louis
  • Yashapal Singh, University of Missouri–St. Louis
  • Tinghua Wang
  • Scott A. Geringer, University of Missouri–St. Louis
  • Keith J Stine, University of Missouri–St. Louis
Abstract
Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.
Disciplines
Publication Date
December 11, 2017
DOI
10.1021/ACS.JOC.7B02768
Citation Information
Alexei Demchenko, Yashapal Singh, Tinghua Wang, Scott A. Geringer, et al.. "Regenerative Glycosylation" The Journal of Organic Chemistry Vol. 83 Iss. 1 (2017) p. 374 - 381
Available at: http://works.bepress.com/alexei-demchenko/156/