(8R,12S)-Yingzhaosu C | 2302-89-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (8R,12S)-Yingzhaosu C
• 英文别名: Yingzhaosu C, (3S-cis)-；2-[(3S,6R)-6-methyl-6-(4-methylphenyl)dioxan-3-yl]propan-2-ol
• CAS: 2302-89-8
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: FCQCSKGBKUYFSW-DZGCQCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基锂 、 (3S,6R)-6-Methyl-6-p-tolyl-[1,2]dioxane-3-carboxylic acid methyl ester 以 乙醚 为溶剂， 反应 0.17h， 以50%的产率得到(8R,12S)-Yingzhaosu C
  参考文献：
  名称：

  Enantioselective Total Syntheses and Stereochemical Studies of All Four Stereoisomers of Yingzhaosu C

  摘要：

  The enantioselective total syntheses and the stereochemistry of all four stereoisomers of yingzhaosu C, an antimalarial peroxy-containing sesquiterpene isolated from yingzhao [Artabotrys uncinatus (L.) Merr.], are described. The key to the syntheses was the combination of Sharpless asymmetric epoxidation and the intramolecular nucleophilic epoxy-opening with a benzylic peroxy group to construct the 1,2-dioxane skeleton. The configurations of the 1,2-dioxanes in four stereoisomers were assigned by spectroscopy and chemical transformation.

  DOI：

  10.1021/jo00115a019

文献信息

• Enantioselective Total Syntheses and Stereochemical Studies of All Four Stereoisomers of Yingzhaosu C
  作者：Xing-Xiang Xu、Han-Qing Dong

  DOI：10.1021/jo00115a019

  日期：1995.5

  The enantioselective total syntheses and the stereochemistry of all four stereoisomers of yingzhaosu C, an antimalarial peroxy-containing sesquiterpene isolated from yingzhao [Artabotrys uncinatus (L.) Merr.], are described. The key to the syntheses was the combination of Sharpless asymmetric epoxidation and the intramolecular nucleophilic epoxy-opening with a benzylic peroxy group to construct the 1,2-dioxane skeleton. The configurations of the 1,2-dioxanes in four stereoisomers were assigned by spectroscopy and chemical transformation.