De novo asymmetric synthesis of the pyranoses-from monosaccharides to oligosaccharides: An update.

The various methods for the de novo asymmetric synthesis of the pyranose sugars are surveyed in this update of the 2013 Advances in Carbohydrate Chemistry and Biochemistry review. The survey begins with a general overview of the various de novo approaches to carbohydrates and defines the use of asymmetric catalysis for the de novo asymmetric synthesis of pyranoses. Next the application to pyranose-containing oligosaccharides is introduced via the use of a palladium-mediated glycosylation. The application of the diastereoselective palladium-catalyzed glycosylation in conjunction with the Achmatowicz approach towards the synthesis of oligosaccharides is presented. Finally, an alternative diastereoselective palladium-catalyzed glycosylation, followed by ring-closing methathesis to oligosaccharides is reviewed.
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