New Synthetic Routes to Carbohydrates by the Use of Telomers of Vinylene Carbonate with Polyhalomethanes
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概要
- 論文の詳細を見る
Type 2 telomers (n=1,2) of vinylene carbonate 1 with polyhalomethanes, carbon tetrachloride and chloroform, were transformed to pentoses (triose) by new route involving two-step conversion of trichloromethyl groups into aldehydes, and tetroses and hexoses by smooth cyanation followed by reductive hydrolysis of trichloromethyls in analogous treatment described for pentoses. Thus DL-arabinose and DL-xylose were prepared in 44% (and 32%) and 43% (and 38%) yields from 5-chloro-5'-trichloromethyl-[4,4'-bi-1,3-dioxolane]-2,2'-dione, 3 and 4 (and 5-trichloromethyl-[4,4'-bi-1,3-dioxolane]-2,2'-dione, 5 and 6), respectively, providing the unamiguous stereochemistry of the n=2 telomers 3 and 4 (and 5 and 6) as trans-"syn"-trans and trans-"anti"-trans configurations. 4-Chloro-5-trichloromethyl-1,3-dioxolan-2-one 13 gave DL-glyceraldehyde, DL-threose and DL-erythrose. DL-Galactose and DL-altrose, and DL-idose and DL-glucose were obtained from the syn form 3,and the anti form 4,respectively.
- 公益社団法人日本薬学会の論文
- 1975-11-25
著者
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滝沢 武夫
Faculty of Pharmaceutical Sciences, University of Tokyo
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國枝 武久
Faculty of Pharmaceutical Sciences, University of Tokyo
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高畑 広紀
Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University
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高畑 広紀
Faculty Of Pharmaceutical Sciences University Of Tokyo
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滝沢 武夫
Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address) Department Of Chemistry Uni
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國枝 武久
Faculty Of Pharmaceutical Sciences Kumamoto University
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