Chemical and Biochemical Studies on Carbohydrate Esters. XIII. Synthesis of 6-O-, 6,6'-Di-O-, and 4,6,4', 6'-Tetra-O-stearoyl-α, α-trehaloses
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概要
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2,3,2', 3'-Tetra-O-benzyl-α, α-trehalose was synthesized conveniently in improved yield according to the known pathway but under modified reaction conditions : namely, α, α-trehalose was treated with α, α-dimethoxytoluene to give its 4,6 : 4', 6'-di-O-benzylidene derivative, which was benzylated with benzyl chloride in dimethylsulfoxide in the presence of sodium hydride, and subsequently debenzylidenated by hydrolysis with 80% acetic acid. Selective acylation of the key intermediate by reaction with 1.4 molar equivalents of stearoyl chloride, followed by catalytic hydrogenolysis over palladium black, afforded 6-O-stearoyl-α, α-trehalose, mp 116-122℃, [α]^<18>_D+108.2°(c=1.0,chloroform), and 6,6'-di-O-stearoyl-α, α-trehalose, mp 157-160℃, [α]^<18>_D+80.8°(c=1.0,chloroform), in an approximate molar ratio of 1 : 3.8. Similarly, 4,6,4', 6'-tetra-O-stearoyl-α, α-trehalose, mp 95-97℃ and 108-110℃ (double melting point), [α]^<17>_D+54.5°(c=1.0,chloroform), was also obtained by the use of 4 molar equivalents of acid chloride. Based on comparison of the carbon-13 nuclear magnetic resonance (^<13>C NMR) spectral data and thin-layer and gas-liquid chromatographic behavior, the major components contained in the monoand diester preparations which had been produced in our previous work by transesterification of α, α-trehalose with methyl stearate and shown to possess interesting biological activities were identified as the 6- and 6,6'-stearates, respectively.
- 社団法人日本薬学会の論文
- 1982-04-25
著者
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西川 嘉廣
Faculty of Pharmaceutical Sciences, Kanazawa University
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吉本 公浩
Faculty of Pharmaceutical Sciences, Kanazawa University
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吉本 公浩
金沢大学薬学部
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西川 嘉廣
金沢大学薬学部
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若宮 貴子
Faculty of Pharmaceutical Sciences, Kanazawa University
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西川 嘉廣
Faculty Of Pharmaceutical Sciences Kanazawa University
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若宮 貴子
Faculty Of Pharmaceutical Sciences Kanazawa University
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