Branched-chain Sugars. IX. Reaction of 3,6-Anhydro-1,2-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose with Nitromethane or Hydrogen Cyanide

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概要

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• 3,6-Anhydro-1,2-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose (2) was converted into 5,6-di-O-acetyl-1, 2-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose (5) by the protection of the carbonyl function with hydroxylamine, followed by acetylation and removal of the protecting group with chromium(II) acetate. Nitromethane condensation of 2 and 5 at room temperature gave the corresponding 3-nitromethyl derivatives having D-gluco- and D-allo-configuration, respectively. The difference in the stereoselectivity was explained by the easiness of isomerization of the initial product to thermodynamically stable epimer, because the reaction temperature was essential to control the selectivity in the same reaction of 1,2 : 5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose. Reaction of 2 with hydrogen cyanide in dry pyridine followed by acetylation gave the corresponding 3,5,6-tri-O-acetyl-3-cyano derivative of D-allo-type, whereas, the reaction in water gave instantly 3-(hydroxycarbonimidoyl)-1,2-O-isopropylidene-α-D-allofuranose 3′,5-lactone, by the participation of the C5-hydroxyl group.

• 日本化学会の論文

著者

• SATO Ken-ichi

  Laboratory of Molecular Biology, Biosignal Research Center, Kobe University

• 佐藤 憲一

  Laboratory of Organic Chemistry, Faculty of Engineering, Kanagawa University

• 吉村 寿次

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

• Sato Ken-ichi

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

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