(2S,3R,4S,6R)-2,3,4-trihydroxy-6-methylcyclohexanone | 1187828-02-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,6R)-2,3,4-trihydroxy-6-methylcyclohexanone
• 英文别名: 4-epi-gabosine B；(2S,3R,4S,6R)-2,3,4-trihydroxy-6-methylcyclohexan-1-one
• CAS: 1187828-02-9
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: FQFXYFNHFVFHPV-GFKUXRSRSA-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：

  2,3,4-tri-O-benzyl-6,7-dideoxy-D-gluco-hept-6-enopyranose 在 五羰基铁 、 palladium on activated charcoal 、 氢气 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 73.0h， 生成 (2S,3R,4S,6R)-2,3,4-trihydroxy-6-methylcyclohexanone
  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

文献信息

• From vinyl pyranoses to carbasugars by an iron-catalyzed reaction complementary to classical Ferrier carbocyclization
  作者：Dinh Hung Mac、Ramesh Samineni、Julien Petrignet、Pabbaraja Srihari、Srivari Chandrasekhar、Jhillu Singh Yadav、René Grée

  DOI：10.1039/b907632h

  日期：——

  Starting from vinylpyranoses an iron-catalyzed tandem isomerization–intramolecular aldolization reaction was developed to prepare cyclohexenone derivatives bearing substituents on the double bond, and it has been applied in a short synthesis of 4-epi-gabosines A and B, from D-glucose.

  从乙烯糖开始，开发了一种以铁催化的串联异构化-分子内醇缩反应，用于制备在双键上带有取代基的环己烯酮衍生物，并已应用于从D-葡萄糖合成4-epi-gabosines A和B的短程合成中。