Natural products and their derivatives have gained much attention from synthetic chemists, biomedical researchers, and even non-scientists. Specifically, polyhydroxylic natural products play many vital roles in human biology and demands for increasing access to polyol derivatives for biomedical research are manifest over the years.   The challenges for synthetic chemists to synthesize these derivatives include the ability to differentiate between similarly reactive hydroxyl groups. Furthermore, the development of safe and efficient methodologies to synthesize these analogs is a priority for synthetic chemists.  Previously, the Gervay-Hague lab found that Regioselective Silyl Exchange Technology (ReSET) could selectively functionalize mono- and di-saccharides and reduce the synthesis steps to increase yield in batch laboratory reactions.  More recently, continuous flow chemistry has been investigated, in which the ability to control heat transfer, rapid mixing and pressure affords increased selectivity and specificity in some reactions. The results of continuous flow studies using ReSET for site-specific conversion of silyl ether polyols to partially-<i>O</i>-acetyl polyols will be presented. Optimizing the reaction conditions using <sup>29</sup>Si NMR increases efficiency.  The data indicate that temperature, concentration, acid catalyst, and resident time can be tuned to achieve site-specific functionalization.

Implementing regioselective silyl exchange technology (ReSET) in continuous flow chemistry to selectively functionalize natural product polyols

Fall 2022 abstracts, posters, and presentations will launch in mid-September.

ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.