(2S,3R,4R,5S,6S,8E)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxyl-2,4,6,8-tetramethyl-dec-8-en-1-al | 1447732-02-6

• 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,3R,4R,5S,6S,8E)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxyl-2,4,6,8-tetramethyl-dec-8-en-1-al
• 英文别名: (E,2S,3R,4R,5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-2,4,6,8-tetramethyl-3-triethylsilyloxydec-8-enal
• CAS: 1447732-02-6
• 化学式: C₂₆H₅₄O₃Si₂
• 分子量: 470.884
• InChiKey: JZFJTTNTZNWBSO-KRBRDFBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.23
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S,6S,8E)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxyl-2,4,6,8-tetramethyl-dec-8-en-1-al 在 1,8-双二甲氨基萘 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2S,3S,4R,5S,6S,8S,11S,12R,13S,14R,15S,16S,18E)-1-(8,15-bis(tert-butyldimethylsilyloxy)-13-triethylsilyloxy-11-methoxy-4-methoxybenzyl)oxy-2,4,6,12,14,16,18-heptamethyl-3,5-[(dimethyl-methylene)dioxy]-icos-18-en-9-one
  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
• 作为产物：
  描述：

  (2R,3S,4R,5S,6S,8E)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxyl-2,4,6,8-tetramethyl-dec-8-en-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以100%的产率得到(2S,3R,4R,5S,6S,8E)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxyl-2,4,6,8-tetramethyl-dec-8-en-1-al
  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

• Stereoselective synthesis of the C13–32 spiroacetal fragment of spirangien A
  作者：Claire Gregg、Michael V. Perkins

  DOI：10.1016/j.tet.2013.06.012

  日期：2013.8

  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.