Reagent controlled β-specific dehydrative glycosylation reactions with 2-deoxy-sugars
John Paul Issa1, Dina Lloyd, Emily Steliotes
1Department of Chemistry, Tufts University, Medford, Massachusetts 02155, USA.
Abstract:
N-Sulfonyl imidazoles activate 2-deoxy-sugar hemiacetals for glycosylation presumably by converting them into glycosyl sulfonates in situ. By matching the leaving group ability of the sulfonate with the reactivity of the donor, it is possible to obtain β-specific glycosylation reactions. The reaction serves as proof of the principle that, by choosing promoters that can modulate the reactivity of active intermediates, it is possible to place glycosylation reactions entirely under reagent control.
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