(2R,3S,4S,5S,6E,8S,9Z)-5-(tert-butyldimethylsilyloxy)-1-(p-methoxybenzyloxy)-4-[(p-methoxyphenyl)diphenylmethoxymethyl]-2,6,8-trimethylundeca-6,9-diene-3-ol | 1032734-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3S,4S,5S,6E,8S,9Z)-5-(tert-butyldimethylsilyloxy)-1-(p-methoxybenzyloxy)-4-[(p-methoxyphenyl)diphenylmethoxymethyl]-2,6,8-trimethylundeca-6,9-diene-3-ol
• CAS: 1032734-17-0
• 化学式: C₄₉H₆₆O₆Si
• 分子量: 779.145
• InChiKey: UHGLNDRDPUNKJW-BOVRHHJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.39
• 重原子数：
  56.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5S,6E,8S,9Z)-5-(tert-butyldimethylsilyloxy)-1-(p-methoxybenzyloxy)-4-[(p-methoxyphenyl)diphenylmethoxymethyl]-2,6,8-trimethylundeca-6,9-diene-3-ol 在 二异丁基氢化铝 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 (2R,3S,4S,5S,6E,8S,9Z)-5-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-4-[(p-methoxyphenyl)diphenylmethoxymethyl]-2,6,8-trimethylundeca-6,9-diene-1-ol
  参考文献：
  名称：

  The Total Synthesis of (+)-Tedanolide

  摘要：

  The first total synthesis of the (+)-tedanolide is described. Pivotal steps are the Felkin-selective aldol coupling between C12 and C13 and an efficient Mitsunobu macrolactonization. Selective protecting group transformations and subsequent oxidations generate the macrocyclic triketone. In the endgame of the synthesis, four TBS groups are removed in one reaction and a chemo- and stereoselective final step epoxidation generates (+)-tedanolide.

  DOI：

  10.1021/ja0659572
• 作为产物：
  描述：

  (2R,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-1-(p-methoxybenzyloxy)-2,6,8-trimethylundeca-6,9-diene-3,5-diol 在 咪唑 、 四丁基氟化铵 作用下， 生成 (2R,3S,4S,5S,6E,8S,9Z)-5-(tert-butyldimethylsilyloxy)-1-(p-methoxybenzyloxy)-4-[(p-methoxyphenyl)diphenylmethoxymethyl]-2,6,8-trimethylundeca-6,9-diene-3-ol
  参考文献：
  名称：

  The Total Synthesis of (+)-Tedanolide

  摘要：

  The first total synthesis of the (+)-tedanolide is described. Pivotal steps are the Felkin-selective aldol coupling between C12 and C13 and an efficient Mitsunobu macrolactonization. Selective protecting group transformations and subsequent oxidations generate the macrocyclic triketone. In the endgame of the synthesis, four TBS groups are removed in one reaction and a chemo- and stereoselective final step epoxidation generates (+)-tedanolide.

  DOI：

  10.1021/ja0659572

文献信息

• The Total Synthesis of (+)-Tedanolide—A Macrocyclic Polyketide from Marine SpongeTedania ignis
  作者：Gunnar Ehrlich、Jorma Hassfeld、Ulrike Eggert、Markus Kalesse

  DOI：10.1002/chem.200701529

  日期：2008.2.27

  Tedanolide, which was isolated by Schmitz in 1984 from the marine sponge Tedania ignis, is a highly cytotoxic macrolide leading to strong growth inhibition of P338 tumor cells in bioassays. A unique structural feature of the known tedanolides is the primary hydroxyl group incorporated in the macrolactone. This unusual motif for macrolactones originated from PKS biosynthesis might arise through lactonizations

  舒达尼在1984年从海棉Tedania ignis分离出的泰达内酯是一种具有高度细胞毒性的大环内酯，在生物测定中可强烈抑制P338肿瘤细胞的生长。已知的四氢大麻酚的独特结构特征是大环内酯中引入的伯羟基。源于PKS生物合成的大内酯的这种不寻常的基序可能是通过内酯化而不是通过硫酯酶反应衍生的内酯化而产生的。在该合成过程中，获得了支持该假说并反映了PKS诱导的大内酯化的内在偏好的第一批实验数据。讨论了形成14元大环化反应的固有偏好以及合成中的关键步骤。