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Continuous synthesis of bromoalkyl glycosides by Fischer glycosylation in a microreactor

Continuous synthesis of bromoalkyl glycosides by Fischer glycosylation in a microreactor In this study, bromoalkyl glycosides were successfully synthesized in microreactor scale by Fischer glycosylation. Yields between 24 and 40% after purification were achieved using various acidic catalysts and conditions. In some experiments, yields 180% higher than with previously known methods could be achieved. This study showed also that reversed-phase flash chromatography is more successful than normal-phase flash chromatography for the purification of bromoalkyl glycosides. Furthermore, longer bromoalcohols were shown to be more compatible than shorter bromoalcohols under these reaction conditions. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

Continuous synthesis of bromoalkyl glycosides by Fischer glycosylation in a microreactor

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Publisher
Springer Journals
Copyright
Copyright © The Author(s) 2021
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1007/s41981-021-00202-0
Publisher site
See Article on Publisher Site

Abstract

In this study, bromoalkyl glycosides were successfully synthesized in microreactor scale by Fischer glycosylation. Yields between 24 and 40% after purification were achieved using various acidic catalysts and conditions. In some experiments, yields 180% higher than with previously known methods could be achieved. This study showed also that reversed-phase flash chromatography is more successful than normal-phase flash chromatography for the purification of bromoalkyl glycosides. Furthermore, longer bromoalcohols were shown to be more compatible than shorter bromoalcohols under these reaction conditions.

Journal

Journal of Flow ChemistrySpringer Journals

Published: Mar 1, 2022

Keywords: Microreactor; Carbohydrates; Fischer glycosylation; Glycosides; Bromides; Linker

References