AI Article Synopsis
- - A continuous flow reactor has been developed to enhance the selectivity of glycosylation reactions specifically for deoxy sugars, optimizing conditions based on the stability of activated intermediates.
- - The combination of the flow reactor with HPLC analysis allows for efficient optimization, achieving significant improvements in the yield of TsCl-mediated -linked deoxy sugar constructions within hours.
- - This method not only enhances the reaction outcomes in continuous flow but also translates to better results in traditional batch-scale reactions, enabling rapid development of selective glycosylation methods when standard techniques aren't feasible.
Article Abstract
The development of a continuous flow reactor for stereospecific glycosylation reactions with deoxy sugars is described. This apparatus that permits optimizing the selectivity of glycosylation reactions based on the stability of the activated intermediate is described. By coupling a flow apparatus with HPLC analysis, we can optimize the yield of TsCl-mediated -linked deoxy sugar construction in a matter of hours. In all cases, results from continuous flow processing translate into improved results in batch-scale reactions, as demonstrated by competition experiments. This is the result of carrying out optimization to identify the ideal temperature for the reaction of the activated intermediate, as opposed to the initial activation conditions. Such an approach allows for the rapid development of highly selective glycosylation reactions in cases in which classical neighboring group participation is not possible.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11448650 | PMC |
| http://dx.doi.org/10.1021/acs.oprd.4c00140 | DOI Listing |
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