(1β,3α,3aα,6α)-3a,6-dimethyl-6-[(2E)-3-(dimethylphenylsilyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)pentyl]-1,2,3,3a,4,5-hexahydro-3-(1-methylethyl)-1-(tert-butyldimethylsilyloxy)-7(6H)-azulenone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1β,3α,3aα,6α)-3a,6-dimethyl-6-[(2E)-3-(dimethylphenylsilyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)pentyl]-1,2,3,3a,4,5-hexahydro-3-(1-methylethyl)-1-(tert-butyldimethylsilyloxy)-7(6H)-azulenone
• 英文别名: (1R,3S,6R,8aR)-3-[tert-butyl(dimethyl)silyl]oxy-6-[(E)-3-[dimethyl(phenyl)silyl]-5-(oxan-2-yloxy)pent-2-enyl]-6,8a-dimethyl-1-propan-2-yl-2,3,7,8-tetrahydro-1H-azulen-5-one
• 化学式: C₃₉H₆₄O₄Si₂
• 分子量: 653.106
• InChiKey: SVCMDEJATSYPIX-NSIIKZCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.76
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(tetrahydro-2H-pyran-2-yloxy)-2-pentyn-1-ol 在 N,N-二甲基丙烯基脲 、 三乙胺 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 生成 (1β,3α,3aα,6α)-3a,6-dimethyl-6-[(2E)-3-(dimethylphenylsilyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)pentyl]-1,2,3,3a,4,5-hexahydro-3-(1-methylethyl)-1-(tert-butyldimethylsilyloxy)-7(6H)-azulenone
  参考文献：
  名称：

  Formal Synthesis of (±)-Guanacastepene A

  摘要：

  A 17 step synthesis of 55, a late intermediate in Danishefsky's guanacastepene A synthesis, has been completed in 4% overall yield. Key features include the use of vinylmagnesium bromide in the Pd-catalyzed coupling with triflate 13 to give triene 16 without the formation of Heck products, a novel extension of the Stork-Jung vinylsilane Robinson annulation that provides tricyclic 2-hydroxymethylcyclohexenone 42 from 23b in four steps and 51% yield, the ability to obtain almost exclusively alpha'-alkylation of 35ba by the proper choice of protecting groups, and the ability to obtain the desired -alcohol selectively by reduction of keto alcohol 42 rather than keto ester 53.

  DOI：

  10.1021/jo026702j

文献信息

• Formal Synthesis of (±)-Guanacastepene A
  作者：Bo Shi、Natalie A. Hawryluk、Barry B. Snider

  DOI：10.1021/jo026702j

  日期：2003.2.1

  A 17 step synthesis of 55, a late intermediate in Danishefsky's guanacastepene A synthesis, has been completed in 4% overall yield. Key features include the use of vinylmagnesium bromide in the Pd-catalyzed coupling with triflate 13 to give triene 16 without the formation of Heck products, a novel extension of the Stork-Jung vinylsilane Robinson annulation that provides tricyclic 2-hydroxymethylcyclohexenone 42 from 23b in four steps and 51% yield, the ability to obtain almost exclusively alpha'-alkylation of 35ba by the proper choice of protecting groups, and the ability to obtain the desired -alcohol selectively by reduction of keto alcohol 42 rather than keto ester 53.