Synthesis of persialylated beta-cyclodextrins |
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Authors: | Roy R Hernández-Mateo F Santoyo-González F |
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Affiliation: | Department of Chemistry, University of Ottawa, Ontario, Canada. rroy@science.uottawa.ca |
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Abstract: | The synthesis of homogeneous hepta-antennated C-6 branched sialosyl cyclomaltoheptose derivatives (persialylated beta-cyclodextrins) has been performed in good to excellent yields, and the compounds have been fully characterized. The thioacetate N-acetylneuraminic acid derivative 6 was selectively de-S-acetylated and coupled by nucleophilic displacement in a one-pot reaction to the heptakis(chloroacetamido) beta-CDs 2 and 5, yielding multivalent sialosides 8 and 9, respectively. The thiourea-linked sialyl-CD 10 was obtained by reaction of the 4-isothiocyanatophenyl N-acetylneuraminic acid derivative 7 with the per-tert-butoxycarbonylamino beta-CD derivative 2 after suitable deprotection of the amino function. |
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