(3R,7S)-1-[2-[(4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methyl-6-tri(propan-2-yl)silyloxyhexyl]-1,3-dioxolan-2-yl]-7-[(2R,3S)-3-[(2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxy]-2-triethylsilyloxypropyl]oxiran-2-yl]-7-[(3-fluorophenyl)methoxy]hept-4-yn-3-ol | 1208257-61-7

• 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: (3R,7S)-1-[2-[(4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methyl-6-tri(propan-2-yl)silyloxyhexyl]-1,3-dioxolan-2-yl]-7-[(2R,3S)-3-[(2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxy]-2-triethylsilyloxypropyl]oxiran-2-yl]-7-[(3-fluorophenyl)methoxy]hept-4-yn-3-ol
• CAS: 1208257-61-7
• 化学式: C₇₅H₁₁₉FO₁₁Si₄
• 分子量: 1328.1
• InChiKey: IPUUXJRVTVIADS-VASJJPJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  91
• 可旋转键数：
  40
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (3R,7S)-1-[2-[(4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methyl-6-tri(propan-2-yl)silyloxyhexyl]-1,3-dioxolan-2-yl]-7-[(2R,3S)-3-[(2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxy]-2-triethylsilyloxypropyl]oxiran-2-yl]-7-[(3-fluorophenyl)methoxy]hept-4-yn-3-ol 、 甲基磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成
  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 Noyori's catalyst 、 异丙醇 作用下， 反应 1.0h， 以86%的产率得到(3R,7S)-1-[2-[(4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methyl-6-tri(propan-2-yl)silyloxyhexyl]-1,3-dioxolan-2-yl]-7-[(2R,3S)-3-[(2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxy]-2-triethylsilyloxypropyl]oxiran-2-yl]-7-[(3-fluorophenyl)methoxy]hept-4-yn-3-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.