Préparation de nouveaux dioxanes chiraux à partir de précurseurs glucidiques

Authors: Robert-Scott, Gabrielle
Advisor: Giguère, Denis
Abstract: To this day, there is still a growing interest from the scientific community towards the discovery of novel molecular scaffolds. In a goal to discover new biologically interesting chemical entities, glycochemistry has compelling benefits. The use of carbohydrates allows to effectively attain important characteristics such as chirality and functionalization. Moreover, carbohydrates are one of the most important class of biomolecules as they contribute to a vast array of biochemical processes. To this day, many of their mechanisms of action still need to be studied; however, these results will certainly make the pharmaceutical field progress. This master's thesis attempts to demonstrate the importance of glycochemistry to facilitate the preparation of heterocycles. Together, heterocyclic and carbohydrate chemistry pose a real interest for medicinal chemistry. The work presented has for goal to illustrate the challenges associated with the synthesis of heterocycles and the importance of glycochemistry in this flourishing field. The identification of an unprecedented heterocyclic framework gave us access to a scaffold with a high density of chirality otherwise difficult to achieve. With the intention of performing synthetic derivatization of this new entity, we first optimized the key annulative dimerization reaction. We then attempted the preparation of different analogues of this scaffold, as well as the synthesis of a variety of glycomimetics from these compounds. The 1,4-dioxane patterns have a rare conformation in the liquid and solid-states. Moreover, this novel class of heterocyclic compounds could demonstrate biological potential. These results could lead the way towards new synthetic tools for medicinal chemistry.
Document Type: Mémoire de maîtrise
Issue Date: 2021
Open Access Date: 19 July 2021
Grantor: Université Laval
Collection:Thèses et mémoires

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