(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 | 1234707-79-9

• 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: (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
• 英文别名: [(4S,5R,7S,8S)-8-[tert-butyl(dimethyl)silyl]oxy-4,7-dimethylnon-1-en-5-yl] (2E,4R,5S,6E,9S)-5-[tert-butyl(dimethyl)silyl]oxy-11-[[tert-butyl(dimethyl)silyl]oxymethyl]-9-[(2R)-2-hydroxy-2-methylbut-3-enoyl]oxy-3,4-dimethyldodeca-2,6,11-trienoate
• CAS: 1234707-79-9
• 化学式: C₄₉H₉₂O₈Si₃
• 分子量: 893.521
• InChiKey: QHHYPWTZMMNXOQ-NKUZYWRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.28
• 重原子数：
  60
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2R)-2-hydroxy-2-methylbut-3-enoic acid 、 (2E,4R,5S,6E,9R)-((4S,5R,7S,8S)-8-(tert-butyldimethylsilyloxy)-4,7-dimethylnon-1-en-5-yl) 5-(tert-butyldimethylsilyloxy)-11-((tert-butyldimethylsilyloxy)methyl)-9-hydroxy-3,4-dimethyldodeca-2,6,11-trienoate 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以72%的产率得到(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
  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

文献信息

• Enantioselective Synthesis of a Diastereomer of Iriomoteolide-1a. What Is the Correct Structure of the Natural Product?
  作者：Lijing Fang、Jiong Yang、Fei Yang

  DOI：10.1021/ol1011423

  日期：2010.7.16

  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.