Correlation Engine 2.0
Clear Search sequence regions

  • carbohydrate (1)
  • donors (1)
  • galactosides (4)
  • oxygen (2)
  • Sizes of these terms reflect their relevance to your search.

    We developed an indirect synthetic method for α-l-fucosides. Based on the fact that l-fucose is 6-deoxy-l-galactose, our strategy consists of the stereoselective construction of α-l-galactoside and its conversion to α-l-fucoside via C6-deoxygenation. The formation of α-l-galactoside is strongly directed using 4,6-O-di-tert-butylsilylene(DTBS)-protected l-galactosyl donors. The DTBS-directed α-l-galactosylation showed broad substrate applicability along with excellent coupling yield and α-selectivity. In the C6-deoxygenation of α-l-galactosides, the Barton-McCombie reaction facilitated the conversion to l-fucosides with good yield. To demonstrate the applicability of our method, we synthesized naturally occurring α-l-fucosides.


    Hirotaka Tomida, Takuya Matsuhashi, Hide-Nori Tanaka, Naoko Komura, Hiromune Ando, Akihiro Imamura, Hideharu Ishida. Indirect synthetic route to α-l-fucosides via highly stereoselective construction of α-l-galactosides followed by C6-deoxygenation. Organic & biomolecular chemistry. 2020 Jul 08;18(26):5017-5033

    Expand section icon Mesh Tags

    Expand section icon Substances

    PMID: 32573638

    View Full Text