Regenerative GlycosylationThe Journal of Organic Chemistry (2017)
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 DateDecember 11, 2017
Citation InformationAlexei 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/