(1S)-1-[(2S,3S)-3-[(2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxy]-2-triethylsilyloxypropyl]oxiran-2-yl]but-3-yn-1-ol | 1208257-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S)-1-[(2S,3S)-3-[(2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxy]-2-triethylsilyloxypropyl]oxiran-2-yl]but-3-yn-1-ol
• CAS: 1208257-58-2
• 化学式: C₄₀H₅₆O₆Si₂
• 分子量: 689.052
• InChiKey: PLHCQMZMMJJPCF-HVIUQXSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.09
• 重原子数：
  48
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S)-1-[(2S,3S)-3-[(2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxy]-2-triethylsilyloxypropyl]oxiran-2-yl]but-3-yn-1-ol 、 3-氟溴苄 在 四丁基硫酸氢铵 、 potassium hydroxide 作用下， 以 水 、 苯 为溶剂， 反应 12.0h， 以82%的产率得到tert-butyl-[(2R)-2-[[(2S,3R)-3-[(1S)-1-[(3-fluorophenyl)methoxy]but-3-ynyl]oxiran-2-yl]methyl]-3-[(4-methoxyphenyl)methoxy]-2-triethylsilyloxypropoxy]-diphenylsilane
  参考文献：
  名称：

  Spirodiepoxide Strategy to the C Ring of Pectenotoxin 4: Synthesis of the C1−C19 Sector

  摘要：

  The synthesis of a C1-C19 precursor to pectenotoxin 4 is presented, The strategy employed the functionalized allene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an allene spirodiepoxidation/C-ring formation cascade.

  DOI：

  10.1021/ol902984e
• 作为产物：
  描述：

  、 (2R,3S)-3-[(2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxy]-2-triethylsilyloxypropyl]oxirane-2-carbaldehyde 以 甲苯 为溶剂， 以80%的产率得到(1S)-1-[(2S,3S)-3-[(2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxy]-2-triethylsilyloxypropyl]oxiran-2-yl]but-3-yn-1-ol
  参考文献：
  名称：

  Spirodiepoxide Strategy to the C Ring of Pectenotoxin 4: Synthesis of the C1−C19 Sector

  摘要：

  The synthesis of a C1-C19 precursor to pectenotoxin 4 is presented, The strategy employed the functionalized allene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an allene spirodiepoxidation/C-ring formation cascade.

  DOI：

  10.1021/ol902984e

文献信息

• Spirodiepoxide Strategy to the C Ring of Pectenotoxin 4: Synthesis of the C1−C19 Sector
  作者：Sipak Joyasawal、Stephen D. Lotesta、N. G. Akhmedov、Lawrence J. Williams

  DOI：10.1021/ol902984e

  日期：2010.3.5

  The synthesis of a C1-C19 precursor to pectenotoxin 4 is presented, The strategy employed the functionalized allene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an allene spirodiepoxidation/C-ring formation cascade.