S-ethyl (2R,3R,4S)-4-(tert-butyldimethylsiloxy)-3-hydroxy-2-methylpentanethioate | 1039034-27-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: S-ethyl (2R,3R,4S)-4-(tert-butyldimethylsiloxy)-3-hydroxy-2-methylpentanethioate
• 英文别名: S-ethyl (2R,3R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2-methylpentanethioate
• CAS: 1039034-27-9
• 化学式: C₁₄H₃₀O₃SSi
• 分子量: 306.542
• InChiKey: NSXGPOJLENOZAA-GRYCIOLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-ethyl (2R,3R,4S)-4-(tert-butyldimethylsiloxy)-3-hydroxy-2-methylpentanethioate 在 三乙基硅烷 、 10% Pd on charcoal 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 (2R,3R,4S)-4-(tert-butyldimethylsiloxy)-3-hydroxy-2-methylpentanal
  参考文献：
  名称：

  Asymmetric Total Synthesis of Botcinins C, D, and F

  摘要：

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.

  DOI：

  10.1021/ol801066y
• 作为产物：
  描述：

  [1-(ethylthio)prop-1-enyloxy]trimethylsilane 、 (S)-2-(叔丁基-二甲基-锡氧基)-丙醛 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 15.67h， 以67%的产率得到S-ethyl (2R,3R,4S)-4-(tert-butyldimethylsiloxy)-3-hydroxy-2-methylpentanethioate
  参考文献：
  名称：

  Asymmetric Total Synthesis of Botcinins C, D, and F

  摘要：

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.

  DOI：

  10.1021/ol801066y

文献信息

• Asymmetric Total Synthesis of Botcinins C, D, and F
  作者：Hiroki Fukui、Isamu Shiina

  DOI：10.1021/ol801066y

  日期：2008.7.17

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.