Effect of 3-Hydroxyl Group on 5,6-Epimine Formation in 1,2-O-Isopropylideneglucofuranose
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概要
- 論文の詳細を見る
Treatment of 6-azido-6-deoxy-1,2-O-isopropylidene-5-O-tosyl-α-D-glucofuranose (6b) or its 3-O-acetyl derivative (6a) with LiAlH_4 in tetrahydrofuran gave a 5,6-epimine (7a) which was characterized as its acetate (8). In comparison with the case of the 3-O-benzyl derivative (2) reported earlier, it was suggested that the free 3-hydroxyl group participates in the substitution of the 5-O-tosyloxy group by the formed 6-amine, decreasing the yield of 5,6-epimine. It was found that treatment of these 6-azido-5-O-tosylates with sodium borohydride and tris (α, α'-dipyridyl) cobalt (II) bromide resulted in formation of the corresponding 6-amino-5-tosylates (10b and 13). Reactions of the latter with bases were also discussed.
- 公益社団法人日本薬学会の論文
- 1969-08-25
著者
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佐伯 博道
Central Research Laboratories, Sankyo Co., Ltd.
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大木 英二
Research Laboratory Zenyaku Kogyo Co. Ltd.
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大木 英二
Central Research Laboratories Sankyo Co. Ltd.
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佐伯 博道
Central Research Laboratories Sankyo Co. Ltd.
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