tert-butyl-[(3S,5S)-5-[(4S,5R,6S)-6-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]hex-1-yn-3-yl]oxy-dimethylsilane | 1447731-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl-[(3S,5S)-5-[(4S,5R,6S)-6-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]hex-1-yn-3-yl]oxy-dimethylsilane
• CAS: 1447731-97-6
• 化学式: C₃₀H₅₀O₅Si
• 分子量: 518.809
• InChiKey: VVXQDULNSMDISG-XCTYBWCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.05
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(3S,5S)-5-[(4S,5R,6S)-6-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]hex-1-yn-3-yl]oxy-dimethylsilane 在 mercury(II) diacetate 、 4-甲基苯磺酸吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 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：

  (3S,5S,6S,7R,9S)-3-(tert-butyldimethylsilyloxy)-6,8-dihydroxy-10-(4-methoxyphenyl)oxy-5,7,9-trimethyl-dec-1-yne 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以24.5 mg的产率得到tert-butyl-[(3S,5S)-5-[(4S,5R,6S)-6-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]hex-1-yn-3-yl]oxy-dimethylsilane
  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.