(2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde | 792922-38-4

• 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: (2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde
• CAS: 792922-38-4
• 化学式: C₂₃H₃₀O₄Si
• 分子量: 398.574
• InChiKey: HVGGQXKHAJUUJH-QIJUGHKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde 在 palladium on activated charcoal chromium dichloride 、 氢气 、 戴斯-马丁氧化剂 、 nickel dichloride 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 tert-Butyl-{(2S,3R,5S)-5-methoxy-3-[1-((1R,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-vinyl]-tetrahydro-furan-2-ylmethoxy}-diphenyl-silane
  参考文献：
  名称：

  Fragmentation of Golgi membranes by norrisolide and designed analogues

  摘要：

  The effect of norrisolide (4) and designed analogues on the Golgi membranes is presented. We found that 4 is the first compound known to induce an irreversible vesiculation of these membranes. To investigate the chemical origins of this new effect we synthesized and evaluated a series of norrisolide analogues in which the chemical functionalities present in the parent structure were altered. Such structure/function studies suggest that the perhydroindane core of 4 is critical for binding to the target protein, while the C21 acetate unit is essential for the irreversible vesiculation of the Golgi membranes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.003
• 作为产物：
  描述：

  (4R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-ethenyloxolan-2-one 在 吡啶 、 lead(IV) acetate 、 盐酸 、 四氧化锇 、 N-甲基吲哚酮 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 13.08h， 生成 (2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde
  参考文献：
  名称：

  Fragmentation of Golgi membranes by norrisolide and designed analogues

  摘要：

  The effect of norrisolide (4) and designed analogues on the Golgi membranes is presented. We found that 4 is the first compound known to induce an irreversible vesiculation of these membranes. To investigate the chemical origins of this new effect we synthesized and evaluated a series of norrisolide analogues in which the chemical functionalities present in the parent structure were altered. Such structure/function studies suggest that the perhydroindane core of 4 is critical for binding to the target protein, while the C21 acetate unit is essential for the irreversible vesiculation of the Golgi membranes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.003

文献信息

• Fragmentation of Golgi membranes by norrisolide and designed analogues
  作者：Thomas P. Brady、Erin K. Wallace、Sun Hee Kim、Gianni Guizzunti、Vivek Malhotra、Emmanuel A. Theodorakis

  DOI：10.1016/j.bmcl.2004.08.003

  日期：2004.10

  The effect of norrisolide (4) and designed analogues on the Golgi membranes is presented. We found that 4 is the first compound known to induce an irreversible vesiculation of these membranes. To investigate the chemical origins of this new effect we synthesized and evaluated a series of norrisolide analogues in which the chemical functionalities present in the parent structure were altered. Such structure/function studies suggest that the perhydroindane core of 4 is critical for binding to the target protein, while the C21 acetate unit is essential for the irreversible vesiculation of the Golgi membranes. (C) 2004 Elsevier Ltd. All rights reserved.