(E)-(3S,4S,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,6-dimethyl-8-triethylsilanyloxy-undeca-1,5-diene | 614754-83-5

• 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: (E)-(3S,4S,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,6-dimethyl-8-triethylsilanyloxy-undeca-1,5-diene
• 英文别名: tert-butyl-[(3S,4S,5E,8R)-3,6-dimethyl-8-triethylsilyloxyundeca-1,5-dien-4-yl]oxy-dimethylsilane
• CAS: 614754-83-5
• 化学式: C₂₅H₅₂O₂Si₂
• 分子量: 440.858
• InChiKey: WGZPLGLPGMGOTE-SACSPNCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.73
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-(3S,4S,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,6-dimethyl-8-triethylsilanyloxy-undeca-1,5-diene 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 氧气 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 三乙胺 、 (+)-二异松蒎基氯硼烷 、 copper(l) chloride 、 palladium dichloride 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 120.0h， 生成 (4R,8R,9R,E)-8-hydroxy-6-methyl-9-((7S,9R)-9-(pent-4-enyl)-6,10-dioxaspiro[4,5]decan-7-yl)dec-6-en-4-yl acetate
  参考文献：
  名称：

  Total Synthesis of Dolabelide D

  摘要：

  The first total synthesis of dolabelide D (or of any of the closely related dolabelides) has been achieved with a longest linear sequence of 17 steps. Key features of the synthesis include an application of the catalytic asymmetric silane alcoholysis, the tandem silylformylation-crotylsilylation, and a Brook-like 1,4-carbon to oxygen silyl migration.

  DOI：

  10.1021/ja058692k
• 作为产物：
  描述：

  (3S,4S,5Z,8R)-6-[tert-butyl(dimethyl)silyl]-3-methyl-8-triethylsilyloxyundeca-1,5-dien-4-ol 、 碘甲烷 在 正丁基锂 、 N,N-二甲基丙烯基脲 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到(E)-(3S,4S,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,6-dimethyl-8-triethylsilanyloxy-undeca-1,5-diene
  参考文献：
  名称：

  Total Synthesis of Dolabelide D

  摘要：

  The first total synthesis of dolabelide D (or of any of the closely related dolabelides) has been achieved with a longest linear sequence of 17 steps. Key features of the synthesis include an application of the catalytic asymmetric silane alcoholysis, the tandem silylformylation-crotylsilylation, and a Brook-like 1,4-carbon to oxygen silyl migration.

  DOI：

  10.1021/ja058692k

文献信息

• Approach to the Synthesis of Dolabelides A and B:  Fragment Synthesis by Tandem Silylformylation−Crotylsilylation
  作者：Darby R. Schmidt、Peter K. Park、James L. Leighton

  DOI：10.1021/ol035431b

  日期：2003.9.1

  [GRAPHICS]A synthesis of the C(15)-C(30) fragment of Dolabelides A and B has been achieved. The recently developed asymmetric silane alcoholysis and tandem silylformylation-crotylsilylation reactions were used as the key steps to establish the C(23)-C(27) 1,5-syn-diol. In addition, the flexibility of this methodology has been demonstrated with an efficient synthesis of the C(24)-C(25) trisubstituted olefin.
• Total Synthesis of Dolabelide D
  作者：Peter K. Park、Steven J. O'Malley、Darby R. Schmidt、James L. Leighton

  DOI：10.1021/ja058692k

  日期：2006.3.1

  The first total synthesis of dolabelide D (or of any of the closely related dolabelides) has been achieved with a longest linear sequence of 17 steps. Key features of the synthesis include an application of the catalytic asymmetric silane alcoholysis, the tandem silylformylation-crotylsilylation, and a Brook-like 1,4-carbon to oxygen silyl migration.