Oligosaccharides play important roles is a variety of physiological processes and are structural components of natural products, pharmaceuticals, and every day materials. Despite their immense importance, only a few methods are available for stereoselective synthesis of 1,2-cis glycosides, a special subclass of saccharides containing a challenging glycosidic linkage. In this presentation we will describe recent developments of a general dehydrative glycosylation method capitalizing on the use of electrophilic phosphonium activators and C1 hemiacetals. Mechanistic studies and applications in the synthesis of bioactive oligosaccharides will be also discussed. These studies are a part of a larger program focused on the use of main group elements in organic synthesis.

New methods and strategies in carbohydrate synthesis

252nd National Meeting (2016)

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