有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
総説および総合論文
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
眞鍋 史乃佐藤 寛子
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ジャーナル 認証あり

2013 年 71 巻 6 号 p. 616-624

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抄録

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.
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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© 2013 社団法人 有機合成化学協会
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