Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
New Synthetic Routes to Carbohydrates by the Use of Telomers of Vinylene Carbonate with Polyhalomethanes
高畑 広紀國枝 武久滝沢 武夫
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ジャーナル フリー

1975 年 23 巻 11 号 p. 3017-3026

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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.
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© The Pharmaceutical Society of Japan
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