(2S,3S,4S)-4-((2S,3S,5S,6R,8S,9R)-5-((tert-butyldimethylsilyl)oxy)-8-((2S,3S,4S,E)-3-((tert-butyldimethylsilyl)oxy)-4,6-dimethyloct-6-en-2-yl)-3,9-dimethyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-1-((4-methoxybenzyl)oxy)-2-methylpentan-3-ol | 1447732-09-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,3S,4S)-4-((2S,3S,5S,6R,8S,9R)-5-((tert-butyldimethylsilyl)oxy)-8-((2S,3S,4S,E)-3-((tert-butyldimethylsilyl)oxy)-4,6-dimethyloct-6-en-2-yl)-3,9-dimethyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-1-((4-methoxybenzyl)oxy)-2-methylpentan-3-ol
• CAS: 1447732-09-3
• 化学式: C₄₇H₈₄O₇Si₂
• 分子量: 817.351
• InChiKey: OKSSGXANIAZEBS-BJCJLLSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.97
• 重原子数：
  56.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (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 在 吡啶 、 水 、 1,8-双二甲氨基萘 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 137.0h， 生成 (2S,3S,4S)-4-((2S,3S,5S,6R,8S,9R)-5-((tert-butyldimethylsilyl)oxy)-8-((2S,3S,4S,E)-3-((tert-butyldimethylsilyl)oxy)-4,6-dimethyloct-6-en-2-yl)-3,9-dimethyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-1-((4-methoxybenzyl)oxy)-2-methylpentan-3-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