Glycosidic bicyclic lactones as new carbohydrate scaffolds

Carboxymethyl glycoside lactone (CMGL) synthons: Scope of the method and preliminary results on step growth polymerization of α-azide-ω-alkyne glycomonomers

“…Offering a straightforward alternative to other methods which lead to 1,2-bisfunctionalized carbohydrate derivatives, the possibility to develop some chemistry at this position was investigated (Scheme 5) [5]. After opening the lactone ring with allyl or propargyl amines, several types of functions can be introduced at OH-2, such as carbamates by reaction with isocyanates, ethers by reaction with halides, or ketones by oxidation.…”

“…The advantages of the method are its generality with respect to many amines, the mild reaction conditions, the easy access to a variety of CMGLs, the fixation of the anomeric stereochemistry at the synthon step instead of the coupling one, and the possibility to further transform the deprotected OH-2 after lactone opening, leading to 1,2-bisfunctionalized systems [5]. The purpose of this article is to give a brief overview of the method as well as preliminary results on a new illustration exploring new types of polymerizable -azide--alkyne glycomonomers in the perspective of obtaining new glycopolymers.…”