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    Tetrahedron Report Number 462 - Recent Advances in StereoselectiveC-Glycoside Synthesis

    Author
    Du, Y.; Linhardt, Robert J.; Vlahov, I.R.
    ORCID
    https://orcid.org/0000-0003-2219-5833
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    Date Issued
    1998
    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
    Tetrahedron Report Number 462 - Recent Advances in StereoselectiveC-Glycoside Synthesis, Y. Du, R.J. Linhardt, I.R. Vlahov, Tetrahedron,54,9913-9961, 1998.
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    URI
    https://doi.org/10.1016/S0040-4020(98)00405-0; https://hdl.handle.net/20.500.13015/5897
    Abstract
    Carbohydrate analogs in which a carbon atom substitutes for the glycosidic oxygen are called Cglycosides. During the last two decades, the synthesis of C-glycosides has become an area of intense study among carbohydrate chemists and biochemists because: 1) The discovery of naturally occurring C-nucleosides with important pharmacological properties I gave impetus to synthetic efforts for preparing active carbohydrate analogs; 2) The requirement of C-glycoside chiral building blocks in the synthesis of biologically important macromolecules, such as palytoxin, 2 spongistatin 3,4 and halichondrin B, 5 has stimulated the development of the new synthetic methodologies; 3) C-glycosides are potential inhibitors of carbohydrate processing enzymes and are stable analogs of glycans involved in important intra- and inter-cellular processes. 6-9 C-glycoside synthesis has been reviewed by Postema, 1° Levy, II Sinay, 12 Beau 13 and Nicotra. 6 The aim of the present survey is to provide a summary of the recent applications, published since 1994, of stereoselective methods in the synthesis of C-glycosides. A generalized overview of the most common synthons and intermediates in the C-glycosylation is shown on Scheme 1. The numbers in italics indicate specific sections in this article that describe each synthetic method presented.;
    Description
    Tetrahedron, 54, 9913-9961; 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/10.1016/S0040-4020(98)00405-0;
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