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Stereoselective synthesis of (+)-5-thiosucrose and (+)-5-thioisosucrose
http://hdl.handle.net/10069/39796
http://hdl.handle.net/10069/3979653c98f38-bcbd-40d6-be01-b43b9b432d83
名前 / ファイル | ライセンス | アクション |
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RSCA10_9730.pdf (778.3 kB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2020-04-09 | |||||
タイトル | ||||||
タイトル | Stereoselective synthesis of (+)-5-thiosucrose and (+)-5-thioisosucrose | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
Ueda, Atsushi
× Ueda, Atsushi× Pi, Jinhong× Makura, Yui× Tanaka, Masakazu× Uenishi, Jun'ichi |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | +)-5-Thiosucrose 1, a novel isosteric sulfur analog of sucrose, was synthesized stereoselectively for the first time via indirect β-d-fructofuranosidation involving selective β-d-psicofuranosidation, followed by stereo-inversion of the secondary hydroxy group at the C-3 position on the furanose ring. Glycosidation of protected 5-Thio-d-glucose with a d-psicofuranosyl donor provided β-d-psicofuranosyl 5-Thio-α-d-glucopyranoside and that with d-fructofuranosyl donor gave α-d-fructofuranosyl 5-Thio-α-d-glucopyranoside. Two anomeric stereocenters of the glycosyl donor and acceptor were controlled correctly to provide a single disaccharide among four possible anomeric isomers in the glycosylation. Conversion of the resulting disaccharides afforded (+)-5-Thiosucrose 1 and (+)-5-Thioisosucrose 2 in excellent yields, respectively. Inhibitory activities of 1 and 2 against α-glucosidase in vitro were also examined. | |||||
書誌情報 |
RSC Advances 巻 10, 号 16, p. 9730-9735, 発行日 2020-03-06 |
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出版者 | ||||||
出版者 | Royal Society of Chemistry | |||||
EISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 20462069 | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | 10.1039/D0RA01033B | |||||
権利 | ||||||
権利情報 | c The Royal Society of Chemistry. Open Access Article. Published on 06 March 2020. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | RSC Advances, 10(16), pp.9730-9735; 2020 |