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Diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols via chirality transfer from a glycosyl donor

Author

Listed:
  • Masamichi Tanaka

    (Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi)

  • Koji Sato

    (Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi)

  • Ryoki Yoshida

    (Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi)

  • Nobuya Nishi

    (Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi)

  • Rikuto Oyamada

    (Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi)

  • Kazuki Inaba

    (Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi)

  • Daisuke Takahashi

    (Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi)

  • Kazunobu Toshima

    (Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi)

Abstract

Chemical desymmetrization reactions of meso-diols are highly effective for the precise and efficient synthesis of chiral molecules. However, even though enzyme-catalyzed desymmetric glycosylations are frequently found in nature, there is no method for highly diastereoselective desymmetric chemical glycosylation of meso-diols. Herein, we report a highly diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols found in myo-inositol 1,3,5-orthoesters using a boronic acid catalyst based on predictions of regioselectivity by density functional theory (DFT) calculations. The enantiotopic hydroxyl groups of the meso-diols are clearly differentiated by the stereochemistry at the C2 position of the glycosyl donor with excellent regioselectivities. In addition, the present method is successfully applied to the synthesis of core structures of phosphatidylinositolmannosides (PIMs) and glycosylphosphatidylinositol (GPI) anchors, and common β-mannoside structures of the LLBM-782 series of antibiotics.

Suggested Citation

  • Masamichi Tanaka & Koji Sato & Ryoki Yoshida & Nobuya Nishi & Rikuto Oyamada & Kazuki Inaba & Daisuke Takahashi & Kazunobu Toshima, 2020. "Diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols via chirality transfer from a glycosyl donor," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-16365-8
    DOI: 10.1038/s41467-020-16365-8
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