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Total Synthesis of the Lipid-Anchor-Attached Core Trisaccharides of Lipoteichoic Acids of Streptococcus pneumoniae and Streptococcus oralis Uo5

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    Total Synthesis of the Lipid-Anchor-Attached Core Trisaccharides of Lipoteichoic Acids of Streptococcus pneumoniae and Streptococcus oralis Uo5
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    Organic Letters

    Cite this: Org. Lett. 2020, 22, 2, 537–541
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    https://doi.org/10.1021/acs.orglett.9b04264
    Published December 30, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    Herein we report an efficient total synthesis of lipid-anchor-appended core trisaccharides of lipoteichoic acids of Streptococcus pneumoniae and Streptococcus oralis Uo5. The key features include the expedient synthesis of the rare sugar 2,4,6-trideoxy-2-acetamido-4-amino-d-Galp building block via one-pot sequential SN2 reactions and the α-selective coupling of d-thioglucoside with the diacyl glycerol acceptor to construct a common disaccharide acceptor, which was utilized in the total synthesis of target molecules 1 and 2.

    Copyright © 2019 American Chemical Society

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    Organic Letters

    Cite this: Org. Lett. 2020, 22, 2, 537–541
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.9b04264
    Published December 30, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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