(4S,5R,7S,8S)-8-(tert-butyldimethylsilyloxy)-4,7-dimethylnon-1-en-5-yl carbonochloridate | 1234707-81-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4S,5R,7S,8S)-8-(tert-butyldimethylsilyloxy)-4,7-dimethylnon-1-en-5-yl carbonochloridate
• 英文别名: [(4S,5R,7S,8S)-8-[tert-butyl(dimethyl)silyl]oxy-4,7-dimethylnon-1-en-5-yl] carbonochloridate
• CAS: 1234707-81-3
• 化学式: C₁₈H₃₅ClO₃Si
• 分子量: 363.013
• InChiKey: DRJXVOCVKCOKRL-YHUYYLMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R,7S,8S)-8-(tert-butyldimethylsilyloxy)-4,7-dimethylnon-1-en-5-yl carbonochloridate 、 (5S,9R,E)-5-((R)-but-3-yn-2-yl)-9-(4-methoxybenzyloxy)-2,2,3,3,14,14,15,15-octamethyl-11-methylene-4,13-dioxa-3,14-disilahexadec-6-ene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以214 mg的产率得到(4R,5S,9R,E)-((4S,5R,7S,8S)-8-(tert-butyldimethylsilyloxy)-4,7-dimethylnon-1-en-5-yl) 5-(tert-butyldimethylsilyloxy)-11-((tert-butyldimethylsilyloxy)methyl)-9-(4-methoxybenzyloxy)-4-methyldodeca-6,11-dien-2-ynoate
  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：

  三光气 、 (4S,5R,7S,8S)-8-(tert-butyldimethylsilyloxy)-4,7-dimethylnon-1-en-5-ol 在 吡啶 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 生成 (4S,5R,7S,8S)-8-(tert-butyldimethylsilyloxy)-4,7-dimethylnon-1-en-5-yl carbonochloridate
  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.