6-epi-gabosine O | 1350433-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-epi-gabosine O
• 英文别名: (2S,3R,4R,6S)-2,3,4-trihydroxy-6-methylcyclohexanone；(2S,3R,4R,6S)-2,3,4-trihydroxy-6-methylcyclohexan-1-one
• CAS: 1350433-98-5
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: FQFXYFNHFVFHPV-ZXMNWKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4R,5R,6S)-4,5,6-tris(benzyloxy)-2-methylcyclohex-2-enone 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以60%的产率得到6-epi-gabosine O
  参考文献：
  名称：

  Total synthesis of gabosines via an iron-catalyzed intramolecular tandem aldol process

  摘要：

  Several gabosines, belonging to polyhydroxy-cyclohexenone and cyclohexanone class of natural products, are synthesized in various stereoforms using an intramolecular iron-catalyzed tandem aldol process. The reaction, which starts from vinylic pyranoses, is compatible with two different OH protecting groups (acetyl and benzyl). Further, like the Ferrier carbocyclisation, it is not sensitive to the stereochemistry of sugar molecules used as precursors: six different gabosine-type molecules have been prepared by this route starting from D-Glucose, D-Mannose, and D-Galactose derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.121