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Regenerative Glycosylation.

Yashapal SinghTinghua WangScott A GeringerKeith J StineAlexei V Demchenko
Published in: The 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.
Keyphrases
  • stem cells
  • mesenchymal stem cells
  • cell therapy
  • tissue engineering