ethyl (2E,4E,7R,10E,15R)-15-[tert-butyl(diphenyl)silyl]oxy-7-methoxy-2-methylhexadeca-2,4,10-trienoate | 189163-39-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (2E,4E,7R,10E,15R)-15-[tert-butyl(diphenyl)silyl]oxy-7-methoxy-2-methylhexadeca-2,4,10-trienoate
• CAS: 189163-39-1
• 化学式: C₃₆H₅₂O₄Si
• 分子量: 576.892
• InChiKey: JEXRAKNDYMVZEO-QYBWSHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.93
• 重原子数：
  41
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2E,4E,7R,10E,15R)-15-[tert-butyl(diphenyl)silyl]oxy-7-methoxy-2-methylhexadeca-2,4,10-trienoate 在 氢氟酸 作用下， 以 正己烷 、 水 、 乙腈 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Total Synthesis of Dolatrienoic Acid:  A Subunit of Dolastatin 14

  摘要：

  The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.

  DOI：

  10.1021/jo962217a
• 作为产物：
  描述：

  1,3,5-戊三醇 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 三氟化硼乙醚 、 四丁基氟化铵 、 碘 、 4-甲基苯磺酸吡啶 、 silica gel 、 sodium hydride 、 对甲苯磺酸 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium iodide 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 二乙二醇二甲醚 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 226.5h， 生成 ethyl (2E,4E,7R,10E,15R)-15-[tert-butyl(diphenyl)silyl]oxy-7-methoxy-2-methylhexadeca-2,4,10-trienoate
  参考文献：
  名称：

  Total Synthesis of Dolatrienoic Acid:  A Subunit of Dolastatin 14

  摘要：

  The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.

  DOI：

  10.1021/jo962217a

文献信息

• Total Synthesis of Dolatrienoic Acid:  A Subunit of Dolastatin 14
  作者：Sylvie Mouné,、Gilles Niel、Magali Busquet、Ian Eggleston、Patrick Jouin

  DOI：10.1021/jo962217a

  日期：1997.5.1

  The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.