Studies on Telomers and Oligomers of Vinylene Carbonate. VII. Facile Synthesis of Trihalogenomethyl-containing Aldo-sugars and Polyalcohols
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概要
- 論文の詳細を見る
Facile routes to trichloromethyl-containing aldoses and polyalcohols from low telomers of vinylenecarbonate with carbon tetrachloride are described. 3,3,3-Trichloro-3-deoxyglyceraldehyde derived from n=1 adduct was dimerized to five-membered 1,3-dioxolane derivative preferentially, in contrast to the corresponding 3,3-dichloro compound which gave the dimer in 1,4-dioxane structure. Three-step procedure involving acetalization followed by removal of cyclic carbonate groups and subsequent deacetalization was mild and selective enough to permit the hydrolysis of n=2 telomers to 5,5,5-trichloro-5-dioxy-DL-lyxose and -xylose in excellent yields, while acid hydrolysis under more drastic conditions (at 100-110°) gave the rearranged 5,5,5-trichloro-3,5-dideoxy-pentosulose in dimeric form exclusively. Reduction of telomers (n=1 and 2) and the derivatives with sodium borohydride gave polyalcohols of the type Cl_3C-(CHOH)_n-H (n=2,3,and 4), among which some compounds showed considerable sedative activities.
- 社団法人日本薬学会の論文
- 1977-02-25
著者
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滝沢 武夫
Faculty of Pharmaceutical Sciences, University of Tokyo
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国枝 武久
Faculty of Pharmaceutical Sciences, University of Tokyo
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松浦 勉
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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国枝 武久
Faculty Of Pharmaceutical Sciences Kumamoto University
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