Unnatural carbohydrate analogs are in demand as mechanistic probes for deciphering the biological functions of complex glycans. In this context, glycan synthesis that involves construction of non-glycoside bonds can expand glycomimetic space beyond that accessible through conventional glycosylation strategies. Herein, we describe an approach to non-glycoside bond synthesis that is based on the reaction of glycosyl crotylating agents and sugar-derived aldehydes. This strategy is illustrated in synthesizing mimics of the Manα1,3[Manα1,6]Man core trisaccharide that comprises a variety of biologically relevant oligosaccharides, including glycans that are implicated in virulence and infectivity of HIV. Accordingly, the reactions of O- and C- linked crotylating agents 2 with aldehydes 1 give crotylation products 3, which can be readily transformed to a variety of O- and C- linked trisaccharides with varying stereochemistry and functionality. Attributes of this methodology are modularity, easy access to the crotylation partners from readily available O- or C- allyl glycosides, and versatility of the crotylation products.

Synthesis of oligosaccharides via construction of non-glycoside linkages

254th National Meeting (2017)

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