Homologation Approaches for the Synthesis and Functionalization of Septanose Carbohydrates

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Homologation Approaches for the Synthesis and Functionalization of Septanose Carbohydrates

Mark Peczuh 1 , Cristin Bosko 1 , Zack Cannone 1 , Aditya Pote 1

1 University Of Connecticut, Storrs, United States

The development of synthetic methods to prepare seven membered-ring, septanoses carbohydrates is a major focus of our research program. Septanoses hold promise as glycomimetics of natural sugars, where binding to target proteins, such as lectins, by mimetics is accompanied by resistance to native glycosyl hydrolases. Here we report on three different methods for the conversion of protected pyranoses to septanoses and their subsequent functionalization to glycosides via reactions from the pyranose literature: the synthesis of septanosyl halides and their use in Koenigs-Knorr glycosylations for the preparation of aryl septanosides; the preparation of oxepines – ring expanded analogs of glycals – and their reactivity in Ferrier reactions; and the synthesis of 3-amino septanosides from protected aldopentoses. The new amino-septanosides are then further derivativized via chemoseletive reactions to make a small library of glycosylated compounds. The underlying theme in all these strategies is that they leverage the stereochemistry and functionality of natural pyranose and furanose sugars as starting materials for synthesis.

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