β-rhamnosidic and β-mannosidic linkages are critical components of bacterial and mammalian glycans. However, the generation of these linkages remains an ongoing challenge for glycoscientists. Our current research focuses on improving our access to these linkages. Recently, we synthesized two novel rhamnosyl donors (electrophiles) containing sulfonyl directing groups as model systems to study β-selectivity in the rhamnose and mannose series. The sulfonyl group was selected because it has been shown to have electronic properties that favor formation of the β-linkages. In this poster we describe the total synthesis of these donors, as well as several preliminary glycosylation reactions with glucose based nucleophiles. Future extension of this methodology to biologically relevant β-rhamnosidic linkages, as well as β-mannosidic linkages will also be discussed.

Evaluation of a new rhamnosidic donor containing a sulfonyl directing group for the formation of beta-rhamnosidic linkages

249th National Meeting (2015)

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