3-[2-[(4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methyl-6-tri(propan-2-yl)silyloxyhexyl]-1,3-dioxolan-2-yl]-N-methoxy-N-methylpropanamide | 1208257-51-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[2-[(4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methyl-6-tri(propan-2-yl)silyloxyhexyl]-1,3-dioxolan-2-yl]-N-methoxy-N-methylpropanamide
• CAS: 1208257-51-5
• 化学式: C₃₀H₆₃NO₆Si₂
• 分子量: 590.004
• InChiKey: WMWHOOYJFUTJDY-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.92
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[2-[(4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methyl-6-tri(propan-2-yl)silyloxyhexyl]-1,3-dioxolan-2-yl]-N-methoxy-N-methylpropanamide 、 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 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以55%的产率得到
  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：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以97%的产率得到3-[2-[(4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methyl-6-tri(propan-2-yl)silyloxyhexyl]-1,3-dioxolan-2-yl]-N-methoxy-N-methylpropanamide
  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.