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      Reagent controlled β-specific dehydrative glycosylation reactions with 2-deoxy-sugars.

      1 , , ,
      Organic letters

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          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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          Author and article information

          Journal
          Org. Lett.
          Organic letters
          1523-7052
          1523-7052
          Aug 16 2013
          : 15
          : 16
          Affiliations
          [1 ] Department of Chemistry, Tufts University, Medford, Massachusetts 02155, USA.
          Article
          10.1021/ol4018547
          23906042
          c504ceb5-01fd-4e22-8036-8a73a520771b
          History

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