Synthesis of sulfonamide-bridged glycomimetics |
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Authors: | Lopez Marie Bornaghi Laurent F Driguez Hugues Poulsen Sally-Ann |
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Institution: | Eskitis Institute, Griffith University, Nathan Campus, Queensland, 4111, Australia. |
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Abstract: | A flexible and short synthesis of sulfonamide-bridged di-, tri-, tetra-, and octasaccharide glycomimetics was accomplished by reaction of glycosyl thioacetates with amino sugar substrates. The chemistry to incorporate the sulfonamide linker in place of a native O-glycosidic bond was broadly scoped, allowing access to head-to-head (1?1) and head-to-tail (1→2), (1→3), (1→4), and (1→6) sulfonamide-bridged glycomimetics. The synthesis proceeds with retention of configuration at the anomeric center and is compatible with variable stereochemical arrangements and with acid- and base-labile protecting groups. |
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