3-Oxoglucuronic Acid. III. Synthesis of 3-Amino-3-deoxy-D-allouronic Acid
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概要
- 論文の詳細を見る
3-Amino-3-deoxy-D-allouronic acid hydrochloride (VII) was synthesized. Barium 3-oxo-1,2-O-isopropylidene-D-glucofuranuronate (IV) was converted into the corresponding phenylhydrazone (V) which was hydrogenated to give the 3-amino compound (VI). Acidic hydrolysis of VI gave VII crystalline. The oxime (IX) of methyl 5-O-acetyl-3-oxo-1,2-O-isopropylidene-D-glucofuranuronate (VIII) was found to undergo stereospecific reduction with lithium aluminum hydride to give 3-amino-3-deoxy-D-allose derivative (IIIb^<14>) predominantly. Displacement at C-3 of methyl 5-O-acetyl-3-O-methanesulfonyl-1,2-O-isopropylidene-D-glucofuranuronate (Ib) with sodium azide and subsequent catalytic hydrogenation gave methyl 5-O-acetyl-3-amino-3-deoxy-1,2-O-isopropylidene-D-allofuranuronate (IIb) in low yield.
- 公益社団法人日本薬学会の論文
- 1968-03-25
著者
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前田 昌子
School of Pharmaceutical Sciences, Showa University
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辻 章夫
School of Pharmaceutical Sciences, Showa University
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木下 俊夫
School of Pharmaceutical Sciences, Kitasato University
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辻 章夫
School Of Pharmaceutical Sciences Showa University
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木下 俊夫
School Of Pharmaceutical Sciences Kitasato University
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