(S)-tert-butyl 3-(2-(tert-butyldimethylsilyloxy)-5-methyl-3-oxohexyl)-1H-indole-1-carboxylate | 1416473-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-tert-butyl 3-(2-(tert-butyldimethylsilyloxy)-5-methyl-3-oxohexyl)-1H-indole-1-carboxylate
• 英文别名: tert-butyl 3-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-5-methyl-3-oxohexyl]indole-1-carboxylate
• CAS: 1416473-40-9
• 化学式: C₂₆H₄₁NO₄Si
• 分子量: 459.701
• InChiKey: CBCJFXNPUHBWBV-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 3-(2-(tert-butyldimethylsilyloxy)-5-methyl-3-oxohexyl)-1H-indole-1-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到(S)-tert-butyl 3-(2-hydroxy-5-methyl-3-oxohexyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Asymmetric total synthesis of (+)-sattazolin

  摘要：

  The first asymmetric total synthesis of the antiviral natural product (+)-sattazolin is reported. The total synthesis allowed for unambiguous assignment of the absolute configuration of the hydroxyl bearing stereocenter. Strategies to circumvent an unanticipated alpha-ketol rearrangement encountered in the final steps are also outlined. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.124
• 作为产物：
  描述：

  (S)-methyl 2-((tert-butyldimethylsilyl)oxy)-3-(1H-indol-3-yl)propanoate 在 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 正庚烷 、 乙腈 为溶剂， 反应 2.25h， 生成 (S)-tert-butyl 3-(2-(tert-butyldimethylsilyloxy)-5-methyl-3-oxohexyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Asymmetric total synthesis of (+)-sattazolin

  摘要：

  The first asymmetric total synthesis of the antiviral natural product (+)-sattazolin is reported. The total synthesis allowed for unambiguous assignment of the absolute configuration of the hydroxyl bearing stereocenter. Strategies to circumvent an unanticipated alpha-ketol rearrangement encountered in the final steps are also outlined. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.124

文献信息

• Asymmetric total synthesis of (+)-sattazolin
  作者：Kevin M. Snyder、Trevor S. Doty、Spencer P. Heins、Aimee L. DeSouchet、Kenneth A. Miller

  DOI：10.1016/j.tetlet.2012.10.124

  日期：2013.1

  The first asymmetric total synthesis of the antiviral natural product (+)-sattazolin is reported. The total synthesis allowed for unambiguous assignment of the absolute configuration of the hydroxyl bearing stereocenter. Strategies to circumvent an unanticipated alpha-ketol rearrangement encountered in the final steps are also outlined. (C) 2012 Elsevier Ltd. All rights reserved.