(2S,3S,4S,6E)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyl-oct-6-en-1-ol | 936946-35-9

• 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: (2S,3S,4S,6E)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyl-oct-6-en-1-ol
• CAS: 936946-35-9
• 化学式: C₁₇H₃₆O₂Si
• 分子量: 300.557
• InChiKey: QWTYPRZQGCFKQN-CWFABOFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,6E)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyl-oct-6-en-1-ol 在 2,6-二甲基吡啶 、 锂硼氢 、 zinc(II) tetrahydroborate 、 邻苯二甲酸二甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (2R,3S,4R,5S,6S,8E)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxyl-2,4,6,8-tetramethyl-dec-8-en-1-ol
  参考文献：
  名称：

  Synthesis of the C23–C32 fragment of spirangien

  摘要：

  The synthesis of the C23-C32 fragment of spirangien A is reported using Evans' alkylation, Evans-Metternich aldol reaction and a substrate controlled stereoselective reduction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.02.081
• 作为产物：
  描述：

  (2R)-(E)-2,4-dimethyl-4-hexenal 在 2,6-二甲基吡啶 、 锂硼氢 、 三氟甲磺酸二丁硼 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (2S,3S,4S,6E)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyl-oct-6-en-1-ol
  参考文献：
  名称：

  Stereoselective synthesis of the C13–32 spiroacetal fragment of spirangien A

  摘要：

  Stereoselective synthesis of an advanced intermediate towards the highly cytotoxic polyketide metabolite spirangien A was achieved. A key step in the synthesis was installation of the C23 stereocentre by a substrate controlled C22-23 aldol reaction. Comparison of this result with previous literature reports suggests that the facial preference of the aldehyde controls the outcome of the C22-23 aldol coupling and depends on the 027/25 protecting groups when reacting with complex ketones, which contain the C17-15 stereochemistry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.012

文献信息

• Electrocyclization of Oxatrienes in the Construction of Structurally Complex Pyranopyridones
  作者：Anna D. Fotiadou、Alexandros L. Zografos

  DOI：10.1021/ol3026457

  日期：2012.11.16

  Application of a tandem Knoevenagel/6 pi-electrocyclization sequence is able to produce highly substituted pyranopyridones from moderate to high yields in a one-step reaction. High diasteroselectivity is observed in some cases and was rationalized on the basis of the thermodynamic control of the evidenced reversibility of a 6 pi-electrocyclization reaction. Numerous examples are provided establishing a novel entry in natural product-like structures of pyranopyridone alkaloids.