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- 橋本 勝
- 弘前大学農学生命科学部
書誌事項
- タイトル別名
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- Synthetic Studies on Oligosaccharide Mimics Carrying Sulfur Atoms in the Pyranose Rings
- ピラノースカン サンソ オ イオウ ゲンシ デ チカン シタ チオオリゴサッカリド ノ ゴウセイ ケンキュウ
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This paper describes the synthetic studies of sulfur substituted oligosaccharides performed in our laboratory. Efficient and α-selective glycosidation reactions with 5-thiopyranoses were realized employing 1-O-trichloroacetimidates of 5-thiopyranoses carrying 2-OΟ-etheral protective groups. These conditions were applied for the synthesis of sulfur substituted maltose and isothiomaltose derivatives. The Pummerer rearrangement of 2, 3-O-isopropylidene protected 1-dehydrothiopyranose oxide was found to proceed at the C 1 position regioselectively to provide 5-thiopyranose derivative. Experiments employing labeled compound revealed the reaction mechanism. Development of 3-cyano-3-tert-butyldimethylsilyl-propyl (CSP group) thioether brought us an successful synthesis of sulfur substituted galacturonic acid. Enzymatic properties of these analogue against endo-glycosidases are also described.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 64 (7), 766-777, 2006
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390001205312933760
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- NII論文ID
- 10017618022
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 8032405
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDL
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- KAKEN
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- 抄録ライセンスフラグ
- 使用不可