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Broadening the Scope of the Reverse Orthogonal Strategy for Oligosaccharide Synthesis

  • Scott A. Geringer
    Scott A. Geringer
    Department of Chemistry and Biochemistry, University of Missouri − St. Louis, One University Boulevard, St. Louis, Missouri 63121, United States
  • Gustavo A. Kashiwagi
    Gustavo A. Kashiwagi
    Department of Chemistry and Biochemistry, University of Missouri − St. Louis, One University Boulevard, St. Louis, Missouri 63121, United States
    Department of Chemistry, Saint Louis University, 3501 Laclede Ave., St. Louis, Missouri 63103, United States
  • , and 
  • Alexei V. Demchenko*
    Alexei V. Demchenko
    Department of Chemistry and Biochemistry, University of Missouri − St. Louis, One University Boulevard, St. Louis, Missouri 63121, United States
    Department of Chemistry, Saint Louis University, 3501 Laclede Ave., St. Louis, Missouri 63103, United States
    *Email: [email protected]
Cite this: J. Org. Chem. 2022, 87, 15, 9887–9895
Publication Date (Web):July 21, 2022
https://doi.org/10.1021/acs.joc.2c00905
Copyright © 2022 American Chemical Society

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    Abstract

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    The reverse orthogonal strategy was invented in 2011 in an attempt to address drawbacks of other strategies for glycan assembly. Different from the classical orthogonal approach that relies on the orthogonality of leaving groups, the reverse strategy is based on orthogonal protecting groups that could be removed during the glycosylation step. This strategy remained largely unexplored due to only one combination of orthogonal protecting groups that would fit into this concept. Reported herein are new orthogonal combinations of leaving and protecting groups that help to streamline the glycan assembly. Also reported is further refinement of the previously reported reaction conditions.

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