(4R,8R,9R,E)-8-((tert-butyldimethylsilyl)oxy)-6,9-dimethyl-10-oxoundec-6-en-4-yl acetate | 614754-85-7

• 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: (4R,8R,9R,E)-8-((tert-butyldimethylsilyl)oxy)-6,9-dimethyl-10-oxoundec-6-en-4-yl acetate
• 英文别名: [(E,4R,8R,9R)-8-[tert-butyl(dimethyl)silyl]oxy-6,9-dimethyl-10-oxoundec-6-en-4-yl] acetate
• CAS: 614754-85-7
• 化学式: C₂₁H₄₀O₄Si
• 分子量: 384.632
• InChiKey: NHFIGHMGBFZLJH-LOKRYCTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,8R,9R,E)-8-((tert-butyldimethylsilyl)oxy)-6,9-dimethyl-10-oxoundec-6-en-4-yl acetate 在 咪唑 、 溶剂黄146 、 三乙胺 、 (+)-二异松蒎基氯硼烷 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.08h， 生成 [(4R,6E,8R,9S,10S,12R)-8,12-bis[[tert-butyl(dimethyl)silyl]oxy]-10-hydroxy-6,9-dimethylheptadeca-6,16-dien-4-yl] acetate
  参考文献：
  名称：

  Approach to the Synthesis of Dolabelides A and B:  Fragment Synthesis by Tandem Silylformylation−Crotylsilylation

  摘要：

  [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.

  DOI：

  10.1021/ol035431b
• 作为产物：
  描述：

  (E)-(3S,4S,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,6-dimethyl-8-triethylsilanyloxy-undeca-1,5-diene 在 吡啶 、 氧气 、 copper(l) chloride 、 palladium dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 生成 (4R,8R,9R,E)-8-((tert-butyldimethylsilyl)oxy)-6,9-dimethyl-10-oxoundec-6-en-4-yl acetate
  参考文献：
  名称：

  Approach to the Synthesis of Dolabelides A and B:  Fragment Synthesis by Tandem Silylformylation−Crotylsilylation

  摘要：

  [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.

  DOI：

  10.1021/ol035431b

文献信息

• 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.