2-(2-triisopropylsilanyloxymethyl-6-trityloxymethyl-tetrahydro-pyran-4-ylidene)-ethanol | 335119-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-(2-triisopropylsilanyloxymethyl-6-trityloxymethyl-tetrahydro-pyran-4-ylidene)-ethanol
• 英文别名: (2Z)-2-[(2R,6S)-2-[tri(propan-2-yl)silyloxymethyl]-6-(trityloxymethyl)oxan-4-ylidene]ethanol
• CAS: 335119-61-4
• 化学式: C₃₇H₅₀O₄Si
• 分子量: 586.887
• InChiKey: XMKFDEKPFIJQBV-IANFZUBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.65
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2-triisopropylsilanyloxymethyl-6-trityloxymethyl-tetrahydropyran-4-ylidene)-acetic acid isopropyl ester 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 1.0h， 以97%的产率得到2-(2-triisopropylsilanyloxymethyl-6-trityloxymethyl-tetrahydro-pyran-4-ylidene)-ethanol
  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.