(3R,4R)-5-<<2-(Trimethylsilyl)ethoxy>methoxy>-3-hydroxy-2,4-dimethyl-1-pentene | 105835-06-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R)-5-<<2-(Trimethylsilyl)ethoxy>methoxy>-3-hydroxy-2,4-dimethyl-1-pentene
• 英文别名: (3S,4R)-3,4-dimethyl-5-(2-trimethylsilylethoxymethoxy)pent-1-en-3-ol
• CAS: 105835-06-1
• 化学式: C₁₃H₂₈O₃Si
• 分子量: 260.449
• InChiKey: OEWYXAFRWTXTED-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  (2R)-2-methyl-3-[(2-trimethylsilyl)ethoxy]methoxy-1-propanal 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.5h， 生成 (3R,4R)-5-<<2-(Trimethylsilyl)ethoxy>methoxy>-3-hydroxy-2,4-dimethyl-1-pentene
  参考文献：
  名称：

  Stereoselective synthesis of the pyrrolizidine alkaloids (-)-integerrimine and (+)-usaramine

  摘要：

  Two routes to the pyrrolizidine alkaloid (-)-integerrimine (1) are described. The first, starting from methyl (R)-(-)-3-hydroxy-2-methylpropionate, proceeded in 19 steps to integerrinecic acid lactone (5) which was transformed to the necic acid derivative 30. The latter was coupled to protected retronecine 31, and the synthesis of 1 was completed by lactonization employing Vedejs' protocol. A second, shorter synthesis of (-)-1 was accomplished via 5, starting from (R)-(+)-beta-citronellol (36). This pathway invoked Katsuki-Sharpless epoxidation of 42 for stereoselective construction of the tertiary alcohol of integerrinecic acid. A parallel sequence proceeding via the stereoisomeric epoxide 44 led to the necic acid segment 75 of the alkaloid (+)-usaramine (2). This acid was coupled to the retronecine borane 82 and then lactonized to 2.

  DOI：

  10.1021/jo00034a017