Oligosaccharides are known to be important in cell-to-cell communication processes that initiate many biological processes. Isolating biologically relevant carbohydrates from biological sources is challenging - as is the chemical synthesis, which inevitably requires multiple steps and protecting group manipulations. A methodology of selective acetylation has been developed to shorten the synthesis of complex oligosaccharides. The reaction uses common chemical reagents under microwave assistance to generate partially acetylated building blocks, which otherwise would take many steps to synthesize via conventional methods. Glycosyl iodides exhibit good reactivity and selectivity during the glycosylation reactions. When incorporated with the reaction of introducing cyclic ethers to the anomeric position, functionalized oligosaccharides can be prepared in a relatively short synthetic route and reasonable yields.

Combining selective acetylation and glycosyl iodide cyclic ether glycosylation to achieve brief syntheses of functionalized oligosaccharides

243rd National Meeting (2012)

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