(4R,8R,9R,12R,E)-8-(tert-butyldimethylsilanyloxy)-12-hydroxy-6,9-dimethyl-10-oxoheptadeca-6,16-dien-4-yl acetate | 614754-86-8

• 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: (4R,8R,9R,12R,E)-8-(tert-butyldimethylsilanyloxy)-12-hydroxy-6,9-dimethyl-10-oxoheptadeca-6,16-dien-4-yl acetate
• 英文别名: [(4R,6E,8R,9R,12R)-8-[tert-butyl(dimethyl)silyl]oxy-12-hydroxy-6,9-dimethyl-10-oxoheptadeca-6,16-dien-4-yl] acetate
• CAS: 614754-86-8
• 化学式: C₂₇H₅₀O₅Si
• 分子量: 482.776
• InChiKey: HLZINOMKLKBLLA-BJJPGTPQSA-N

物化性质

• 沸点：
  535.2±50.0 °C(Predicted)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,8R,9R,12R,E)-8-(tert-butyldimethylsilanyloxy)-12-hydroxy-6,9-dimethyl-10-oxoheptadeca-6,16-dien-4-yl acetate 在 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 101.0h， 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：

  (E)-(3R,4R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-3,6-dimethyl-undec-5-en-2-one 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 (+)-二异松蒎基氯硼烷 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (4R,8R,9R,12R,E)-8-(tert-butyldimethylsilanyloxy)-12-hydroxy-6,9-dimethyl-10-oxoheptadeca-6,16-dien-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

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.