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    National Tsing Hua University Institutional Repository > 理學院 > 化學系 > 期刊論文 >  Facile Cu(OTf)(2)-catalyzed preparation of per-O-acetylated hexopyranoses with stoichiometric acetic anhydride and sequential one-pot anomeric substitution to thioglycosides under solvent-free conditions


    Please use this identifier to cite or link to this item: http://nthur.lib.nthu.edu.tw/dspace/handle/987654321/56580


    Title: Facile Cu(OTf)(2)-catalyzed preparation of per-O-acetylated hexopyranoses with stoichiometric acetic anhydride and sequential one-pot anomeric substitution to thioglycosides under solvent-free conditions
    Authors: Tai CA;Kulkarni SS;Hung SC
    教師: 洪上程
    Date: 2003
    Publisher: American Chemical Society
    Relation: JOURNAL OF ORGANIC CHEMISTRY, American Chemical Society, Volume 68, Issue 22, OCT 31 2003, Pages 8719-8722
    Keywords: SCOPE
    ESTERS
    DERIVATIVES
    ALCOHOLS
    ACID ANHYDRIDES
    EFFICIENT CATALYST
    REGIOSELECTIVE ACYLATION
    ACTIVE ACYLATION CATALYST
    OLIGOSACCHARIDE SYNTHESIS
    SCANDIUM TRIFLUOROMETHANESULFONATE
    Abstract: Solvent-free per-O-acetylation of hexoses with a stoichiometric amount of acetic anhydride employing 0.03 mol % Cu(OTf)(2) proceeded in high yields (90-99%) at room temperature to give exclusively pyranosyl products as an anomeric mixture, the alpha/beta ratio of which was dependent on the temperature and amount of catalyst used. Sequential anomeric substitution with p-thiocresol in the presence of BF3.etherate gave the thioglycosides, isolated exclusively or predominantly as one anomer in 66-75% yields.
    URI: http://pubs.acs.org/
    http://nthur.lib.nthu.edu.tw/dspace/handle/987654321/56580
    Appears in Collections:[化學系] 期刊論文

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