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    New approaches to stereocontrolled glycosylation.

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    Thesis embargoed until 09-04-2016 (4.373Mb)
    Singh_G_Use_of_thesis_form_2015.pdf (90.16Kb)
    Author
    Singh, Govind Pratap
    Date
    2015
    Permanent Link
    http://hdl.handle.net/10092/11126
    Thesis Discipline
    Chemistry
    Degree Grantor
    University of Canterbury
    Degree Level
    Doctoral
    Degree Name
    Doctor of Philosophy

    The conceptually simple process of linking carbohydrate units by glycosylation has proven to be one of the most difficult synthetic processes to control from a stereochemical perspective. In particular it is the stereocontrolled synthesis of 1,2-cis glycosyl linkages (e.g. α-glucosides, β-mannosides) which poses the most difficult challenge. The research presented in this thesis describes new ways in which stereocontrol in glycosylation reactions can be achieved. New methods of neighbouring group participation have been explored, utilising novel protecting groups at the 2-postion of a series of glycosyl donors. In particular the use of glucosyl donors bearing a 2-O-(2-(2,4,6- trimethoxyphenyl)thio)ethyl protecting group at the 2-hydroxyl, have shown exceptional α-selectivity especially when a completely armed donor was used. Work within this thesis also describes the use of chiral Brønsted acid catalysts in stereoselective glycosylation reactions. However the yields and stereoselectivity obtained were not very encouraging.

    Subjects
    carbohydrate
     
    glycosylation
     
    stereoselective
     
    NGP
     
    organocatalysis
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    • Science: Theses and Dissertations [3296]
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    http://library.canterbury.ac.nz/thesis/etheses_copyright.shtml

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