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Activation of glycosyl trichloroacetimidates with perchloric acid on silica (HClO4-SiO2) provides enhanced alpha-selectivity

  1. Author:
    Ludek, O. R.
    Gu, W. L.
    Gildersleeve, J. C.

  2. Author Address

    [Ludek, Olaf R.; Gu, Wenlu; Gildersleeve, Jeffrey C.] NCI, Biol Chem Lab, NIH, Frederick, MD 21702 USA.;Gildersleeve, JC, NCI, Biol Chem Lab, NIH, 376 Boyles St, Frederick, MD 21702 USA.;gildersj@mail.nih.gov
    1. Year: 2010
    2. Date: Sep 23
    3. Epub Date: 8/10/2010
  2. Journal: Carbohydrate Research
    1. 345
    2. 14
    3. Pages: 2074-2078
  4. Type of Article: Article
  5. ISSN: 0008-6215
  1. Abstract:

    Obtaining high stereoselectivity in glycosylation reactions is often challenging in the absence of neighboring group participation. In this study, we demonstrate that activation of glycosyl trichloroacetimidate donors with immobilized perchloric acid on silica (HClO4-SiO2) provides higher alpha-selectivity than trimethylsilyl triflate (TMSOTf) for reactions that do not involve neighboring group participation. Published by Elsevier Ltd.

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External Sources

  1. View Full Text
  2. DOI: 10.1016/j.carres.2010.07.030
  3. PMID: 20692651
  4. PMCID: PMC2933952
  5. View record in Web of Science®
  6. WOS: 000283481500012
  7. NIHMSID: Nihms224302

Library Notes

  1. Fiscal Year: FY2009-2010
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