書誌事項
- タイトル別名
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- Isopropylidenation of Maltitol and a New Synthetic Approach for Disaccharides Having an α-Glycosidic Linkage
- マルチトールのイソプロピリデン化反応とα-グリコシド結合を持つ2糖類の新合成経路
- マルチトール ノ イソプロピリデンカ ハンノウ ト アルファ -グリコシド ケ
- Isopropylidenation of Maltitol and a New Synthetic Approach for Disaccharides Having an α-Glycosidic Linkage
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説明
Isopropylidenation of maltitol by using excess 2, 2-dimethoxypropane (DMP) and p-toluenesulfonic acid in N, N-dimethylformamide at room temperature for 15 h yielded four acetals which were designated 1 to 4 in the order of decreasing Rf value on thin layer chromatography. After column chromatography on silica gel, compounds 1-4 were separated as 4, 6 : 1', 2' : 5', 6'-triacetal (1, 14%), 4, 6 : 2', 3' : 5', 6'-triacetal (2, 40%), 1', 2' : 5', 6'-diacetal (3, 4%), and 2', 3' : 5', 6'-diacetal (4, 12%), respectively. Excess DMP or prolonged reaction time results in an acetal migration from 1', 2'-to 2', 3'-positions. The reaction and the yields of 1-4 were investigated by high performance liquid chromatography analysis of the benzoylated acetals. 2', 3'-Di-O-benzylmaltose and 3-O-α-D-glucopyranosyl-β-L-gulopyranose were synthesized after chemical modification of 2 and 4, respectively. Thus, maltitol acetals have a potential value in the synthesis of disaccharides with an α-glycosidic linkage.
収録刊行物
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- 薬学雑誌
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薬学雑誌 108 (11), 1046-1055, 1988
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282681131811456
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- NII論文ID
- 110003648608
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- NII書誌ID
- AN00284903
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- ISSN
- 13475231
- 00316903
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- NDL書誌ID
- 3213567
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