tert-butyldimethyl((2S,3S)-3-methylpent-4-en-2-yloxy)silane | 1234707-91-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyldimethyl((2S,3S)-3-methylpent-4-en-2-yloxy)silane
• CAS: 1234707-91-5
• 化学式: C₁₂H₂₆OSi
• 分子量: 214.423
• InChiKey: XWKKIBKPPCUQDK-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  tert-butyldimethyl((2S,3S)-3-methylpent-4-en-2-yloxy)silane 在 硼烷四氢呋喃络合物 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以11.4 g的产率得到(3S,4S)-4-(tert-butyldimethylsilyloxy)-3-methylpentanal
  参考文献：
  名称：

  Enantioselective Syntheses of the Proposed Structures of Cytotoxic Macrolides Iriomoteolide-1a and -1b

  摘要：

  Enantioselective total syntheses of the proposed structures of macrolide cytotoxic agents iriomoteolide-1a and -1b have been accomplished. The synthesis was carried out in a convergent and stereoselective manner. However, the present work suggests that the reported structures have been assigned incorrectly. The synthesis features Julia-Kocienski olefination, Sharpless asymmetric epoxidation, Brown asymmetric crotylboration, a Sakurai reaction, an aldol reaction, and enzymatic resolution as the key steps.

  DOI：

  10.1021/ol101105v
• 作为产物：
  描述：

  (2S,3S)-3-甲基-4-戊烯-2-醇 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyldimethyl((2S,3S)-3-methylpent-4-en-2-yloxy)silane
  参考文献：
  名称：

  Enantioselective Syntheses of the Proposed Structures of Cytotoxic Macrolides Iriomoteolide-1a and -1b

  摘要：

  Enantioselective total syntheses of the proposed structures of macrolide cytotoxic agents iriomoteolide-1a and -1b have been accomplished. The synthesis was carried out in a convergent and stereoselective manner. However, the present work suggests that the reported structures have been assigned incorrectly. The synthesis features Julia-Kocienski olefination, Sharpless asymmetric epoxidation, Brown asymmetric crotylboration, a Sakurai reaction, an aldol reaction, and enzymatic resolution as the key steps.

  DOI：

  10.1021/ol101105v

文献信息

• Enantioselective Synthesis of a Diastereomer of Iriomoteolide-1a. What Is the Correct Structure of the Natural Product?
  作者：Lijing Fang、Jiong Yang、Fei Yang

  DOI：10.1021/ol1011423

  日期：2010.7.16

  An enantioselective approach to a diastereomer of iriomoteolide-1a is described. Highlighted is a Sml(2)-mediated intramolecular reductive cyclization approach to complex cyclic hemiketals. An acetylide-chloroformate coupling strategy is also featured. Our results show that the structures of iriomoteolide-1a-1c require careful reassessment.