Phenanthroline-Catalyzed Stereoretentive Glycosylations.

ABSTRACT: Carbohydrates are essential moieties of many bioactive molecules in nature. However, efforts to elucidate their modes of action are often impeded by limitations in synthetic access to well-defined oligosaccharides. Most of the current methods rely on the design of specialized coupling partners to control selectivity during the formation of glycosidic bonds. Reported herein is the use of a commercially available phenanthroline to catalyze stereoretentive glycosylation with glycosyl bromides. The method provides efficient access to α-1,2-cis glycosides. This protocol has been performed for the large-scale synthesis of an octasaccharide adjuvant. Density-functional theory calculations, together with kinetic studies, suggest that the reaction proceeds by a double S_N 2 mechanism.

SUBMITTER: Yu F 

PROVIDER: S-EPMC6513695 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature