Many antimicrobial natural products possess unusual sugars that are required for their bioactivity. In contrast to mammalian sugars, however, systematic studies to understand the basis of selectivity in glycosylation reactions with these unusual sugars are limited. As part of a program for developing diastereoselective glycosylation reactions with unusual sugars, we had previously demonstrated that sulfonyl chlorides promote b-selective dehydrative glycosylation reactions. Notably, we had found that the reactivity of the intermediate sulfonate leaving group and the donor sugar had to be matched to obtain selective reactions. This talk will focus on how this information can be used to predict the optimal sulfonyl chloride promoter to use in reactions with previously unstudied glycosyl donors. In addition, cases where this chemistry led to unexpected highly a-selective reactions will be presented, and the mechanistic basis for this change in selectivity will be discussed.

Towards predictable S<sub>N</sub>2 glycosylations using glycosyl sulfonates

ACS Spring Meeting 2021

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Towards predictable SN2 glycosylations using glycosyl sulfonates

Towards predictable S_N2 glycosylations using glycosyl sulfonates