(2S,3E,5S)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,4-dimethylhept-3-en-1ol | 875439-63-7

• 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: (2S,3E,5S)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,4-dimethylhept-3-en-1ol
• 英文别名: (E,2S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-7-[(4-methoxyphenyl)methoxy]-2,4-dimethylhept-3-en-1-ol
• CAS: 875439-63-7
• 化学式: C₂₃H₄₀O₄Si
• 分子量: 408.654
• InChiKey: UJWPZUPCRUAYRL-BMYIBGGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3E,5S)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,4-dimethylhept-3-en-1ol 在 N-乙基哌啶 、 2,6-二甲基吡啶 、 tin(II) trifluoromethanesulfonate 、 三甲基铝 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 正己烷 、 正庚烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.33h， 生成 (E,3S,4S,7S)-3,7-bis[[tert-butyl(dimethyl)silyl]oxy]-9-[(4-methoxyphenyl)methoxy]-4,6-dimethylnon-5-enal
  参考文献：
  名称：

  Synthesis of the N-Acetylcysteamine Thioester of seco-Proansamitocin

  摘要：

  The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.

  DOI：

  10.1021/ol052588q
• 作为产物：
  描述：

  (E,4S)-ethyl-5-(tert-butyldiphenylsilyloxy)-2,4-dimethyl-2-pentenoate 在 N-乙基哌啶 、 2,6-二甲基吡啶 、 sodium hydroxide 、 锂硼氢 、 tin(II) trifluoromethanesulfonate 、 trityl tetrafluoroborate 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 20.17h， 生成 (2S,3E,5S)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,4-dimethylhept-3-en-1ol
  参考文献：
  名称：

  Synthesis of the N-Acetylcysteamine Thioester of seco-Proansamitocin

  摘要：

  The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.

  DOI：

  10.1021/ol052588q

文献信息

• Synthesis of the <i>N</i>-Acetylcysteamine Thioester of <i>s</i><i>eco</i>-Proansamitocin
  作者：Thomas Frenzel、Marco Brünjes、Monika Quitschalle、Andreas Kirschning

  DOI：10.1021/ol052588q

  日期：2006.1.1

  The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.