(3R,4E,7S,8R,11E,13R,14S,15E,18S)-14-(tert-butyldimethylsilyloxy)-8-((2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylbutyl)-18-(2-((tert-butyldimethylsilyloxy)methyl)allyl)-3-hydroxy-3,7,12,13-tetramethyl-1,9-dioxacyclooctadeca-4,11,15-triene-2,10-dione | 1234707-88-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (3R,4E,7S,8R,11E,13R,14S,15E,18S)-14-(tert-butyldimethylsilyloxy)-8-((2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylbutyl)-18-(2-((tert-butyldimethylsilyloxy)methyl)allyl)-3-hydroxy-3,7,12,13-tetramethyl-1,9-dioxacyclooctadeca-4,11,15-triene-2,10-dione
• CAS: 1234707-88-0
• 化学式: C₄₇H₈₈O₈Si₃
• 分子量: 865.467
• InChiKey: AFSYIYGMXDKHQI-USWVKHMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.48
• 重原子数：
  58.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3R,4E,7S,8R,11E,13R,14S,15E,18S)-14-(tert-butyldimethylsilyloxy)-8-((2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylbutyl)-18-(2-((tert-butyldimethylsilyloxy)methyl)allyl)-3-hydroxy-3,7,12,13-tetramethyl-1,9-dioxacyclooctadeca-4,11,15-triene-2,10-dione 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到(3R,4E,7S,8R,11E,13R,14S,15E,18S)-14-(tert-butyldimethylsilyloxy)-8-((2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylbutyl)-3-hydroxy-18-(2-(hydroxymethyl)allyl)-3,7,12,13-tetramethyl-1,9-dioxacyclooctadeca-4,11,15-triene-2,10-dione
  参考文献：
  名称：

  Enantioselective Synthesis of a Diastereomer of Iriomoteolide-1a. What Is the Correct Structure of the Natural Product?

  摘要：

  An enantioselective approach to a diastereomer of iriomoteolide-1a is described. Highlighted is a Sml(2)-mediated intramolecular reductive cyclization approach to complex cyclic hemiketals. An acetylide-chloroformate coupling strategy is also featured. Our results show that the structures of iriomoteolide-1a-1c require careful reassessment.

  DOI：

  10.1021/ol1011423
• 作为产物：
  描述：

  (2E,4R,5S,6E,9S)-((4S,5R,7S,8S)-8-(tert-butyldimethylsilyloxy)-4,7-dimethylnon-1-en-5-yl) 5-(tert-butyldimethylsilyloxy)-11-((tert-butyldimethylsilyloxy)methyl)-9-((R)-2-hydroxy-2-methylbut-3-enoyloxy)-3,4-dimethyldodeca-2,6,11-trienoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以62%的产率得到(3R,4E,7S,8R,11E,13R,14S,15E,18S)-14-(tert-butyldimethylsilyloxy)-8-((2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylbutyl)-18-(2-((tert-butyldimethylsilyloxy)methyl)allyl)-3-hydroxy-3,7,12,13-tetramethyl-1,9-dioxacyclooctadeca-4,11,15-triene-2,10-dione
  参考文献：
  名称：

  Enantioselective Synthesis of a Diastereomer of Iriomoteolide-1a. What Is the Correct Structure of the Natural Product?

  摘要：

  An enantioselective approach to a diastereomer of iriomoteolide-1a is described. Highlighted is a Sml(2)-mediated intramolecular reductive cyclization approach to complex cyclic hemiketals. An acetylide-chloroformate coupling strategy is also featured. Our results show that the structures of iriomoteolide-1a-1c require careful reassessment.

  DOI：

  10.1021/ol1011423