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β-Selective 2-Deoxy- and 2,6-Dideoxyglucosylations Catalyzed by Bis-Thioureas

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    β-Selective 2-Deoxy- and 2,6-Dideoxyglucosylations Catalyzed by Bis-Thioureas
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 40, 27318–27323
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    https://doi.org/10.1021/jacs.4c11560
    Published September 30, 2024
    Copyright © 2024 American Chemical Society
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    Abstract

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    We present methods for β-selective 2-deoxy- and 2,6-dideoxyglucosylations of natural products, carbohydrates, and amino acids using bis-thiourea hydrogen-bond-donor catalysts. Disarming ester protecting groups were necessary to counter the high reactivity of 2-deoxyglycosyl electrophiles toward non-stereospecific SN1 pathways. Alcohol and phenol nucleophiles with both base- and acid-sensitive functionalities were compatible with the catalytic protocol, enabling access to a wide array of 2-deoxy-β-O-glucosides.

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    • Experimental procedures and characterization data for catalyst synthesis, substrate synthesis, and glycosylations; procedures and data for mechanistic studies and additional substrates not shown in scope figures (PDF)

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 40, 27318–27323
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.4c11560
    Published September 30, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

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