2,3-O-isopropylidene-6-deoxy-β-L-arabino-2-hexulofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-6-deoxy-β-L-arabino-2-hexulofuranose
• 英文别名: (3aR,5S,6S,6aR)-3a-(hydroxymethyl)-2,2,5-trimethyl-6,6a-dihydro-5H-furo[2,3-d][1,3]dioxol-6-ol
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: SNKXJFOZSBOBJJ-XZMZPDFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-鼠李糖 、 丙酮 在 sodium aluminate 、 Dowex 50 W (H+) ion-exchange resin 、 硫酸 作用下， 以 水 为溶剂， 反应 50.0h， 以21%的产率得到2,3-O-isopropylidene-6-deoxy-β-L-arabino-2-hexulofuranose
  参考文献：
  名称：

  Base catalysed isomerisation of aldoses of the arabino and lyxo series in the presence of aluminate

  摘要：

  Base-catalysed isomerisation of aldoses of the arabino and lyxo series in aluminate solution has been investigated. L-Arabinose and D-galactose give L-erythro-2-pentulose (L-ribulose) and D-lyxo-2-hexulose (D-tagatose), respectively, in good yields, whereas lower reactivity is observed for 6-deoxy-D-galactose (D-fucose). From D-lyxose, D-mannose and 6-deoxy-L-mannose (L-rhamnose) are obtained mixtures of ketoses and C-2 epimeric aldoses. Small amounts of the 3-epimers of the ketoses were also formed. 6-Deoxy-L-arabino-2-hexulose (6-deoxy-L-fructose) and 6-deoxy-L-glucose (L-quinovose) were formed in low yields from 6-deoxy-L-mannose and isolated as their O-isopropylidene derivatives. Explanations of the differences in reactivity and course of the reaction have been suggested on the basis of steric effects. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00065-4

文献信息

• Base catalysed isomerisation of aldoses of the arabino and lyxo series in the presence of aluminate
  作者：Dag Ekeberg、Svein Morgenlie、Yngve Stenstrøm

  DOI：10.1016/s0008-6215(02)00065-4

  日期：2002.4

  Base-catalysed isomerisation of aldoses of the arabino and lyxo series in aluminate solution has been investigated. L-Arabinose and D-galactose give L-erythro-2-pentulose (L-ribulose) and D-lyxo-2-hexulose (D-tagatose), respectively, in good yields, whereas lower reactivity is observed for 6-deoxy-D-galactose (D-fucose). From D-lyxose, D-mannose and 6-deoxy-L-mannose (L-rhamnose) are obtained mixtures of ketoses and C-2 epimeric aldoses. Small amounts of the 3-epimers of the ketoses were also formed. 6-Deoxy-L-arabino-2-hexulose (6-deoxy-L-fructose) and 6-deoxy-L-glucose (L-quinovose) were formed in low yields from 6-deoxy-L-mannose and isolated as their O-isopropylidene derivatives. Explanations of the differences in reactivity and course of the reaction have been suggested on the basis of steric effects. (C) 2002 Elsevier Science Ltd. All rights reserved.