Synthesis of Sialic Acid Analogues with the Oxime Group at C-4 Or C-5 of KDN 1 |
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| Authors: | Toshitsugu Kai Xue-Long Sun Hiroaki Takayanagi Kimio Furuhata |
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| Affiliation: | School of Pharmaceutical Sciences, Kitasato University , 5-9-1 Shirokane, Minato-ku, Tokyo, 108, Japan |
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| Abstract: | Abstract The readily available methyl (methyl 3-deoxy-5,8:7,9-di-O-isopropylidene-β-D-glycero-D-galacto-2-nonulopyranosid)onate (7) was converted in five synthetic steps into methyl (methyl 4-acetamido-3,4-dideoxy-β-D-glycero-D-talo-2-nonulopyranosid)onate (11). Selective protection of the C-4, C-7, C-8 and C-9 hydroxy groups of methyl (methyl 3-deoxy-8,9-O-isopropylidene-β-D-glycero-D-galacto-2-nonulpyranosid)onate (2) followed by oxidation of the C-5 hydroxy group and then its oximination gave 5-hydroxyimino derivatives (15 and 16). |
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