S-ethyl (3S,5S,7S)-7-{[tert-butyl(diphenyl)silyl]oxy}-5-methoxy-3-methyldecanethioate | 1017238-08-2

• 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: S-ethyl (3S,5S,7S)-7-{[tert-butyl(diphenyl)silyl]oxy}-5-methoxy-3-methyldecanethioate
• 英文别名: S-ethyl (3S,5S,7S)-7-[tert-butyl(diphenyl)silyl]oxy-5-methoxy-3-methyldecanethioate
• CAS: 1017238-08-2
• 化学式: C₃₀H₄₆O₃SSi
• 分子量: 514.845
• InChiKey: UNJQGCCEXBZNBJ-GSDHBNRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-ethyl (3S,5S,7S)-7-{[tert-butyl(diphenyl)silyl]oxy}-5-methoxy-3-methyldecanethioate 在 三乙基硅烷 、 10% Pd/C 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以95%的产率得到(3S,5S,7S)-7-(tert-butyldiphenylsilyloxy)-5-methoxy-3-methyldecanal
  参考文献：
  名称：

  Formal Total Synthesis of Neopeltolide

  摘要：

  A concise synthesis of the core structure of the macrolide neopeltolide was developed featuring a Prins cyclization to fashion the pyran ring. Key steps in the synthesis of aldehyde 16 were a Leighton allylation and a Feringa-Minnaard asymmetric methyl cuprate addition to an unsaturated thioester. For lactonization, a classical Yamaguchi macrolactonization was used. The longest linear sequence consists of 17 steps providing lactone 26 with an overall yield of 23%.

  DOI：

  10.1021/ol8001255
• 作为产物：
  描述：

  S-ethyl (2E,5S,7S)-7-{[tert-butyl(diphenyl)silyl]oxy}-5-methoxydec-2-enethioate 、 甲基溴化镁 在 copper(I) bromide dimethylsulfide complex 、 (R,S)-Josiphos 作用下， 以 乙醚 、 甲基叔丁基醚 为溶剂， 反应 15.17h， 以93%的产率得到S-ethyl (3S,5S,7S)-7-{[tert-butyl(diphenyl)silyl]oxy}-5-methoxy-3-methyldecanethioate
  参考文献：
  名称：

  Formal Total Synthesis of Neopeltolide

  摘要：

  A concise synthesis of the core structure of the macrolide neopeltolide was developed featuring a Prins cyclization to fashion the pyran ring. Key steps in the synthesis of aldehyde 16 were a Leighton allylation and a Feringa-Minnaard asymmetric methyl cuprate addition to an unsaturated thioester. For lactonization, a classical Yamaguchi macrolactonization was used. The longest linear sequence consists of 17 steps providing lactone 26 with an overall yield of 23%.

  DOI：

  10.1021/ol8001255

文献信息

• Formal Total Synthesis of Neopeltolide
  作者：Viktor V. Vintonyak、Martin E. Maier

  DOI：10.1021/ol8001255

  日期：2008.3.1

  A concise synthesis of the core structure of the macrolide neopeltolide was developed featuring a Prins cyclization to fashion the pyran ring. Key steps in the synthesis of aldehyde 16 were a Leighton allylation and a Feringa-Minnaard asymmetric methyl cuprate addition to an unsaturated thioester. For lactonization, a classical Yamaguchi macrolactonization was used. The longest linear sequence consists of 17 steps providing lactone 26 with an overall yield of 23%.