Sugar Acetylene for New Stereocontrolled Synthesis

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概要

• 論文の詳細を見る

• C-Glycosidation is of great significance since it contains the introduction of carbon chains to sugar chirons or sugar nuclei as chiral pools. Silylacetylenes are sufficiently reactive to form sugar acetylenes for the selective introduction of acetylenic groups to sugar rings. Bis-C-glycosidation allows introduction of two sugars at both ends of a bis (trimethylsilyl) acetylene. A 2, 3-dideoxyglucose derivative provided the corresponding C-1 α acetylenic compounds, which would increase the scope of C-glycosidation with silylacetylenes. An alkynyl group attached to the anomeric position of a pyranose ring was epimerized through a dicobalthexacarbonyl complex by treatment with trifluoromethane sulfonic acid. Three steps involving cobalt complexation, acidic transformation and decomplexation afforded overall epimerization and thus prompted us to provide either the α or β alkynyl C-glycoside as desired. Ring opening of a dihydropyran derivative using Nicholas-type cation intermediates was also an accomplished part of this study.

• 社団法人 有機合成化学協会の論文

著者

• ISOBE Minoru

  Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University

• Isobe Minoru

  Laboratory Of Organic Chemistry Bioagricultural Sciences Nagoya University

• Isobe Minoru

  Laboratory of Organic Chemistry, School of Agricultural Sciences, Nagoya University

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