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.
Highlights
Carbohydrates play a major role in a multitude of biological processes and procedures, for example in signaling, cell–cell communication, and molecular and cellular targeting [1, 2]
A promising approach for this is the production of bromoalkyl glycosides in a continuously operated microreactor [18]
In experiment number 6, methoxyethanol could be detected after purification. This is an indication that the 2-bromoethanol in the normal phased (NP) column reacts with the methanol-containing solvent
Summary
Carbohydrates play a major role in a multitude of biological processes and procedures, for example in signaling, cell–cell communication, and molecular and cellular targeting [1, 2]. In the experiments in which 10-bromo-1-decanol was used as the bromoalcohol, yields were achieved exceeding more than 180% compared to other methods. 1 Institute of Precision Medicine, Medical and Life Sciences Faculty, Furtwangen University, Jakob‐Kienzle‐Str. 17, 78054 VS‐Schwenningen, Germany
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