Easy Access to L-Mannosides and L-Galactosides by Using C[BOND]H Activation of the Corresponding 6-Deoxysugars

Authors

  • Tobias Gylling Frihed,

    1. Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø (Denmark)
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  • Mads Heuckendorff,

    1. Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø (Denmark)
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  • Dr. Christian Marcus Pedersen,

    Corresponding author
    1. Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø (Denmark)
    • Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø (Denmark)
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  • Prof. Dr. Mikael Bols

    Corresponding author
    1. Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø (Denmark)
    • Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø (Denmark)
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  • This work was supported by the Lundbeck Foundation.

Abstract

original image

Rare sugars by CH activation: The title compounds have been prepared from the corresponding 6-deoxysugars by an intramolecular C[BOND]H activation in high yields. Diethyl silane is attached to the 4-OH group followed by formation of a Si[BOND]C bond; both transformations are catalyzed by iridium in a one-pot fashion. The subsequent Fleming–Tamao oxidation provided the L-sugars.

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