Unique Reactivity of Pyranosides with 2,3-<i>trans</i> Carbamate Group; Renaissance of Endocyclic Cleavage Reaction

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  • 2,3-<i>trans</i>カーバメート基を持つ糖構造の特異な反応性：糖化学におけるエンド開裂反応の再発見
  • 2,3-transカーバメート基を持つ糖構造の特異な反応性 : 糖化学におけるエンド開裂反応の再発見
  • 2,3-trans カーバメートキ オ モツ トウ コウゾウ ノ トクイ ナ ハンノウセイ : トウカガク ニ オケル エンドカイレツハンノウ ノ サイハッケン
  • Unique Reactivity of Pyranosides with 2,3-trans Carbamate Group; Renaissance of Endocyclic Cleavage Reaction

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Abstract

1,2-cis amino glycosides are often found in biologically active oligosaccharides. For the stereoselective formation of 1,2-cis aminoglycosides, glycosyl donors with 2,3-trans carbamate group were developed. The first synthesis of anti-Helicobacter pylori oligosaccharide was achieved by using the novel glycosyl donor in an effective manner. Furthermore, the pyranosides with 2,3-trans carbamate groups were found to undergo endocyclic cleavage reactions, which are rarely found in pyranosides. The endocyclic cleavage reaction was confirmed both from experimental and computational approaches.<BR>As an additional example of cooperative work of experimental and computational chemistry, understanding of the solvent effect in glycosylation reactions was also described.

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