1 research outputs found
Regenerative Glycosylation
Previously, we communicated 3,3-difluoroxindole
(HOFox)-mediated
glycosylations wherein 3,3-difluoro-3<i>H</i>-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