trifluoro-methanesulfonic acid 4-[2-(tert-butyl-diphenylsilanyloxy)-ethylidene]-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl methyl ester | 184174-50-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: trifluoro-methanesulfonic acid 4-[2-(tert-butyl-diphenylsilanyloxy)-ethylidene]-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl methyl ester
• 英文别名: [(2S,4E,6R)-4-[2-[tert-butyl(diphenyl)silyl]oxyethylidene]-6-[tri(propan-2-yl)silyloxymethyl]oxan-2-yl]methyl trifluoromethanesulfonate
• CAS: 184174-50-3
• 化学式: C₃₅H₅₃F₃O₆SSi₂
• 分子量: 715.034
• InChiKey: XXUDEUFCEZKAID-DYOKQEMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  trifluoro-methanesulfonic acid 4-[2-(tert-butyl-diphenylsilanyloxy)-ethylidene]-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl methyl ester 在 咪唑 、 六甲基磷酰三胺 、 四丁基氟化铵 、 叔丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 51.08h， 生成 [6-(2-{2-(tert-butyl-dimethyl-silanyloxy)-3-[6-(2-(tert-butyl-diphenyl-silanyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1,1-dimethyl-propyl}-[1,3]dithian-2-ylmethyl)-4-(2-tert-butyl-diphenyl-silanyloxy)-ethylidene)-tetrahydropyran-2-yl]-methanol
  参考文献：
  名称：

  Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins

  摘要：

  [GRAPHICS]Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence), Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.

  DOI：

  10.1021/ol015551o
• 作为产物：
  描述：

  2-(2-triisopropylsilanyloxymethyl-6-trityloxymethyl-tetrahydro-pyran-4-ylidene)-ethanol 在 咪唑 、 2,6-二叔丁基-4-甲基吡啶 、 zinc dibromide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 trifluoro-methanesulfonic acid 4-[2-(tert-butyl-diphenylsilanyloxy)-ethylidene]-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl methyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins

  摘要：

  [GRAPHICS]Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence), Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.

  DOI：

  10.1021/ol015551o

文献信息

• Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins
  作者：A. Vakalopoulos、T. F. J. Lampe、H. M. R. Hoffmann

  DOI：10.1021/ol015551o

  日期：2001.3.1

  [GRAPHICS]Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence), Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.