SYNTHESIS OF SOME DEOXY, UNSATURATED, AND DIDEOXY SUGARS VIA REGIOSELECTIVE THIOACYLATION OF GLYCOPYRANOSIDES BY THE DIBUTYLTIN OXIDE METHOD
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概要
- 論文の詳細を見る
Treatment of non-protected glycopyranosides (Me α-D-Glc, Me β-D-Glc, Me α-D-Xyl, and Me β-D-Xyl) with dibutyltin oxide followed by thioacylation with phenoxythiocarbonyl chloride gave the mono-thiono-carbonates regioselectively in high yields. Acetylation of the latter followed by deoxygenation with Bu_3SnH smoothly gave the corresponding deoxy derivatives except for the 6-O___--thionocarbonate derivatives. Similar treatment of the pyranosides that have a cis-vicinal glycol (Me α-D-Gal, Me β-D-Gal, Me β-L-Ara, and Ph α-L-Ara) leads to the formation of cyclic thionocarbonates which on acetylation followed by olefination with trimethylphosphite afforded the unsaturated derivatives in satisfactory yields. On deacetylation and subsequent hydrogenation over platinic oxide, they gave the corresponding dideoxy compounds quantitatively.
- 社団法人日本薬学会の論文
- 1986-01-25
著者
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津田 喜典
金沢大学
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津田 喜典
Faculty of Pharmaceutical Sciences, Kanazawa University
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菊地 徹
Research Institute For Wakan-yaku (oriental Medicines) Toyama Medical And Pharmaceutical University
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津田 喜典
金沢大学薬学部
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津田 喜典
Faculty Of Pharmaceutical Sciences Kanazawa University
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Haque Md.
Research Institute for Wakanyaku (Oriental Medicines), Toyama Medical and Pharmaceutical University
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金光 公浩
Faculty of Pharmaceutical Sciences, Kanazawa University
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Haque Md.
Research Institute For Wakanyaku (oriental Medicines) Toyama Medical And Pharmaceutical University
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菊地 徹
Research Institute For Wakanyaku (oriental Medicines) Toyama Medical And Pharmaceutical University
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金光 公浩
Faculty Of Pharmaceutical Sciences Kanazawa University
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