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Umpolung Reactivity in the Stereoselective Synthesis of S-Linked 2-Deoxyglycosides

Authors

  • Kedar N. Baryal,

    1. Department of Chemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, OH 43606 (USA)
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  • Danyang Zhu,

    1. Department of Chemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, OH 43606 (USA)
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  • Dr. Xiaohua Li,

    1. Department of Chemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, OH 43606 (USA)
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  • Prof. Dr. Jianglong Zhu

    Corresponding author
    1. Department of Chemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, OH 43606 (USA)
    • Department of Chemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, OH 43606 (USA)
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  • Presented in part at the 244th American Chemical Society National Meeting, Philadelphia, PA, USA, August 19–23, 2012, CARB-13. We are very grateful to the National Science Foundation (CHE-1213352) and the University of Toledo for supporting this research. We thank Professors Peter Andreana and Steve Sucheck for proofreading this manuscript and Joseph Duffey, Hanin Dughayli, and Mallory Walker for experimental assistance.

Abstract

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Alles unter Kontrolle: Eine ungewöhnliche Sulfenylierung von stereochemisch definierten 2-Desoxyglycosyllithiumspezies mit asymmetrischen Zuckerdisulfid-Akzeptoren ermöglichte die stereoselektive Synthese von α- sowie β-S-verknüpften 2-Desoxyoligosacchariden. Die reduktive Lithiierung der 2-Desoxyglycosylphenylsulfide bei −78 °C liefert axiale Glycosyllithiumspezies, die beim Erwärmen in die äquatorialen Spezies isomerisieren (siehe Schema).

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