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Allyl Protecting Group Mediated Intramolecular Aglycon Delivery (IAD) of Glycosyl Fluorides

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Timely Research Perspectives in Carbohydrate Chemistry

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Summary

Stereospecific 1,2-cis-glycosylation of 2-O-allyl protected glucosyl and mannosyl fluorides can be achieved via a sequence of allyl isomerization, N-iodosuccinimide mediated tethering, and intramolecular aglycon delivery (IAD). Fluoride is advantageous as an anomeric leaving group since extended reaction times can be employed to tether hindered aglycon alcohols without competitive anomeric activation. Tin(II) chloride mediated intramolecular glycosylation furnishes the desired α-glucosides and β-mannosides in an entirely stereoselective manner.

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Author information

Authors and Affiliations

  1. Dyson Perrins Laboratory, University of Oxford, Oxford, OX1 3QY, UK

    Ian Cumpstey & Antony J. Fairbanks

  2. GlaxoSmithKline, Medicines Research Centre, Stevenage, SG1 2NY, UK

    Alison J. Redgrave

Authors
  1. Ian Cumpstey
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  2. Antony J. Fairbanks
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  3. Alison J. Redgrave
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Editor information

Editors and Affiliations

  1. Institute of Organic Chemistry, University of Vienna, Vienna, Austria

    Walther Schmid

  2. Institute of Organic Chemistry, Technical University of Graz, Graz, Austria

    Arnold E. Stütz

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© 2002 Springer-Verlag Wien

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Cumpstey, I., Fairbanks, A.J., Redgrave, A.J. (2002). Allyl Protecting Group Mediated Intramolecular Aglycon Delivery (IAD) of Glycosyl Fluorides. In: Schmid, W., Stütz, A.E. (eds) Timely Research Perspectives in Carbohydrate Chemistry. Springer, Vienna. https://doi.org/10.1007/978-3-7091-6130-2_6

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  • DOI: https://doi.org/10.1007/978-3-7091-6130-2_6

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-7289-6

  • Online ISBN: 978-3-7091-6130-2

  • eBook Packages: Springer Book Archive

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