(1R,2Z,4Z)-1-{(2R,3R,4E)-3-(2-{[(allyloxyl)carbonyl]amino}ethyl)-5-[(2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-2-hydroxy-3-[(trimethylsilyl)oxy]pent-4-enyl}-5-{(1R,3S)-3-[(4-methoxyphenoxy)methyl]cyclohexyl}penta-2,4-dienyl phenoxyacetate | 521274-45-3

• 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: (1R,2Z,4Z)-1-{(2R,3R,4E)-3-(2-{[(allyloxyl)carbonyl]amino}ethyl)-5-[(2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-2-hydroxy-3-[(trimethylsilyl)oxy]pent-4-enyl}-5-{(1R,3S)-3-[(4-methoxyphenoxy)methyl]cyclohexyl}penta-2,4-dienyl phenoxyacetate
• CAS: 521274-45-3
• 化学式: C₄₈H₆₅NO₁₂Si
• 分子量: 876.129
• InChiKey: VCRQJLBCFCFFSA-DNYXRWFTSA-N

物化性质

• 沸点：
  901.5±65.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.42
• 重原子数：
  62.0
• 可旋转键数：
  25.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  157.31
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (1R,2Z,4Z)-1-{(2R,3R,4E)-3-(2-{[(allyloxyl)carbonyl]amino}ethyl)-5-[(2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-2-hydroxy-3-[(trimethylsilyl)oxy]pent-4-enyl}-5-{(1R,3S)-3-[(4-methoxyphenoxy)methyl]cyclohexyl}penta-2,4-dienyl phenoxyacetate 在 四氮唑 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 2.41h， 生成 [(1S,3R)-3-[(1Z,3Z,5R,7R,8R,9E)-7-bis(prop-2-enoxy)phosphoryloxy-10-[(2S,3S)-3-ethyl-6-oxo-2,3-dihydropyran-2-yl]-5-(2-phenoxyacetyl)oxy-8-[2-(prop-2-enoxycarbonylamino)ethyl]-8-trimethylsilyloxydeca-1,3,9-trienyl]cyclohexyl] (6S)-6-methyloctanoate
  参考文献：
  名称：

  Total Synthesis of Leustroducsin B

  摘要：

  A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).

  DOI：

  10.1021/ja0340679
• 作为产物：
  描述：

  (1R,2Z,4Z)-1-{(2R,3R,4E)-3-(2-{[(allyloxyl)carbonyl]amino}ethyl)-5-[(2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-2,3-dihydroxypent-4-enyl}-5-{(1R,3S)-3-[(4-methoxyphenoxy)methyl]cyclohexyl}penta-2,4-dienyl phenoxyacetate 在 吡啶 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 (1R,2Z,4Z)-1-{(2R,3R,4E)-3-(2-{[(allyloxyl)carbonyl]amino}ethyl)-5-[(2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-2-hydroxy-3-[(trimethylsilyl)oxy]pent-4-enyl}-5-{(1R,3S)-3-[(4-methoxyphenoxy)methyl]cyclohexyl}penta-2,4-dienyl phenoxyacetate
  参考文献：
  名称：

  Total Synthesis of Leustroducsin B

  摘要：

  A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).

  DOI：

  10.1021/ja0340679