(3S,5S,7R,9R,11S,13S,15R,17R)-2,2,6,6,10,10,14,14,18,18-decamethylnonadecane-1,3,5,7,9,11,13,15,17,19-decol | 268750-49-8

• 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: (3S,5S,7R,9R,11S,13S,15R,17R)-2,2,6,6,10,10,14,14,18,18-decamethylnonadecane-1,3,5,7,9,11,13,15,17,19-decol
• CAS: 268750-49-8
• 化学式: C₂₉H₆₀O₁₀
• 分子量: 568.789
• InChiKey: KLRUYOSBAMDLHV-OUMJIQPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  202
• 氢给体数：
  10
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-甲氧基丙烯 、 (3S,5S,7R,9R,11S,13S,15R,17R)-2,2,6,6,10,10,14,14,18,18-decamethylnonadecane-1,3,5,7,9,11,13,15,17,19-decol 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以52%的产率得到(4SR,6RS)-2,2,5,5-tetramethyl-4-[(4RS,6SR)-2,2,5,5-tetramethyl-6-{(4SR,6RS)-2,2,5,5-tetramethyl-6-[(4RS)-2,2,5,5-tetramethyl-1,3-dioxan-4-ylmethyl]1,3-dioxan-4-ylmethyl}-1,3-dioxan-4-ylmethyl]-6-[(4SR)-2,2,5,5-tetramethyl-1,3-dioxan-4-ylmethyl]-1,3-...
  参考文献：
  名称：

  Stereoselective Synthesis of Skipped Polyols by Substrate-Directed Asymmetric Induction

  摘要：

  A series of C-2- or sigma-symmetric oligo-1,3-dioxanylmethanes, 2-5, have been prepared using a bidirectional approach. In bidirectional syntheses of meso compounds, only substrate-based asymmetric induction could be applied. 1,3-Asymmetric induction in Mukaiyama-aldol additions, 1,5-asymmetric induction in enol-borinate aldol reactions, and 1,3-anti-selective reduction of aldols turned out to be reliable tools in the preparation of compounds 3-5.

  DOI：

  10.1021/ol0056325
• 作为产物：
  描述：

  (2S,4R,6S)-4,6-Diallyl-2-(4-methoxy-phenyl)-5,5-dimethyl-[1,3]dioxane 在 palladium dihydroxide 三氟化硼乙醚 、 氯代二环己基硼烷 、 氢气 、 臭氧 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 255.0h， 生成 (3S,5S,7R,9R,11S,13S,15R,17R)-2,2,6,6,10,10,14,14,18,18-decamethylnonadecane-1,3,5,7,9,11,13,15,17,19-decol
  参考文献：
  名称：

  Stereoselective Synthesis of Skipped Polyols by Substrate-Directed Asymmetric Induction

  摘要：

  A series of C-2- or sigma-symmetric oligo-1,3-dioxanylmethanes, 2-5, have been prepared using a bidirectional approach. In bidirectional syntheses of meso compounds, only substrate-based asymmetric induction could be applied. 1,3-Asymmetric induction in Mukaiyama-aldol additions, 1,5-asymmetric induction in enol-borinate aldol reactions, and 1,3-anti-selective reduction of aldols turned out to be reliable tools in the preparation of compounds 3-5.

  DOI：

  10.1021/ol0056325

文献信息

• Conformational Analysis ofoligo-1,3-Dioxanylmethanes
  作者：Thomas Trieselmann、Reinhard W. Hoffmann、Karsten Menzel

  DOI：10.1002/1099-0690(200204)2002:7<1292::aid-ejoc1292>3.0.co;2-6

  日期：2002.4

  Stereoselective synthesis of a series of 1,3-dioxan-4-ylmethanes 1−9 has been achieved by use of solely substrate-based asymmetric induction. The simple C2-symmetric bis(dioxanyl)methane 1 has a greater than 99% conformational preference at the two inter-ring bonds for the conformation 1a. The homologous structures 3−9 contain up to five dioxanylmethane units, maintaining a high conformational preference

  一系列 1,3-二恶烷-4-基甲烷 1-9 的立体选择性合成已通过仅使用基于底物的不对称诱导实现。简单的 C2 对称双（二氧杂环己基）甲烷 1 在构象 1a 的两个环间键处具有大于 99% 的构象偏好。同源结构 3-9 包含多达五个二恶烷基甲烷单元，在每个双（二恶烷基）甲烷单元中保持高构象偏好。因此，这些柔性化合物在多达八个可旋转的环间键上达到超过 90% 的构象偏好。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)