(S)-1-((3R,6R)-6-Methyl-6-p-tolyl-[1,2]dioxan-3-yl)-ethane-1,2-diol | 162302-82-1

• 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: (S)-1-((3R,6R)-6-Methyl-6-p-tolyl-[1,2]dioxan-3-yl)-ethane-1,2-diol
• 英文别名: (1S)-1-[(3R,6R)-6-methyl-6-(4-methylphenyl)dioxan-3-yl]ethane-1,2-diol
• CAS: 162302-82-1
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: IRGKOEPLJOFPOC-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-((3R,6R)-6-Methyl-6-p-tolyl-[1,2]dioxan-3-yl)-ethane-1,2-diol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (2S,3R,6R)-6-p-Tolyl-heptane-1,2,3,6-tetraol
  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
• 作为产物：
  描述：

  Acetic acid (S)-2-hydroxy-2-((R)-6-methyl-6-p-tolyl-[1,2]dioxan-3-yl)-ethyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (S)-1-((3R,6S)-6-Methyl-6-p-tolyl-[1,2]dioxan-3-yl)-ethane-1,2-diol 、 (S)-1-((3R,6R)-6-Methyl-6-p-tolyl-[1,2]dioxan-3-yl)-ethane-1,2-diol
  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