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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
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.
Publication Date
December 11, 2017
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
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