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    Regioselective Synthesis of L-Idopyranuronic Acid Derivatives:Intermolecular Aglycone Transfer Under Standard Glycosylation Conditions

    Author
    Du, Y.; Linhardt, Robert J.
    ORCID
    https://orcid.org/0000-0003-2219-5833
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    Date Issued
    1997
    Subject
    Biology; Chemistry and chemical biology; Chemical and biological engineering; Biomedical engineering
    Degree
    Terms of Use
    In Copyright : this Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). https://rightsstatements.org/page/InC/1.0/;
    Full Citation
    Regioselective Synthesis of L-Idopyranuronic Acid Derivatives:Intermolecular Aglycone Transfer Under Standard Glycosylation Conditions,Y. Du, R.J. Linhardt, Journal of Carbohydrate Chemistry, 16,1327-1344, 1997.
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    URI
    https://doi.org/10.1080/07328309708005753; https://hdl.handle.net/20.500.13015/5908
    Abstract
    C-1-thioacetalization of L-idofuranurono-6,3-lactone followed by regioselective p-methoxybenzylidenation at C-2 and C-4 gave the hydroxylactones 4 and 19, which were protected at C-5 with TBDMS. Lactone ring opening with methylamine followed by regioselective reductive cleavage of the 1,3-dioxane furnished acceptors 9 and 24. Intermolecular ethyl and phenyl thio group transfers were observed during the attempted preparation of disaccharide 35 through coupling reactions of either 9 or 24 with trichloroacetimidate donor 33, leading to the formation of thioglycoside of donor 33 and the thioglycoside of acceptors 9 or 24 in the furanose form. This intermolecular aglycon transfer was investigated under various glycosylation conditions. Finally, the free 4-hydroxyl groups in acceptors 9 and 24 were acetylated. Desilylation at C-5 followed by ring closure with mercuric salts afforded, in both cases, the IdopA donor and/or acceptor precursor 16.;
    Description
    Journal of Carbohydrate Chemistry, 16,1327-1344; Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
    Department
    The Linhardt Research Labs.; The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS);
    Relationships
    The Linhardt Research Labs Online Collection; Rensselaer Polytechnic Institute, Troy, NY; https://harc.rpi.edu/;
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    https://login.libproxy.rpi.edu/login?url=https://doi.org/10.1080/07328309708005753;
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