methyl (E,5S,6R,7S,9S,10R)-10-(2,5-dimethoxy-3-nitrophenyl)-6,7,10-trimethoxy-5,9-dimethyldec-3-enoate | 170707-53-6

• 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: methyl (E,5S,6R,7S,9S,10R)-10-(2,5-dimethoxy-3-nitrophenyl)-6,7,10-trimethoxy-5,9-dimethyldec-3-enoate
• CAS: 170707-53-6
• 化学式: C₂₄H₃₇NO₉
• 分子量: 483.559
• InChiKey: IEJOKWLVWYFYDC-MAEDFGSNSA-N

物化性质

• 沸点：
  554.9±50.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (E,5S,6R,7S,9S,10R)-10-(2,5-dimethoxy-3-nitrophenyl)-6,7,10-trimethoxy-5,9-dimethyldec-3-enoate 在 lead(IV) acetate 、 四氧化锇 、 N-甲基吲哚酮 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (E)-(4S,5R,6S,8S,9R)-9-(2,5-Dimethoxy-3-nitro-phenyl)-5,6,9-trimethoxy-2,4,8-trimethyl-non-2-en-1-ol
  参考文献：
  名称：

  Total Synthesis of Herbimycin A

  摘要：

  Herbimycin A (HA) belongs to a class of antibiotics known as the benzoquinoid ansamycins. Members of this class have shown promising biological activity as Hsp90 inhibitors. An enantioselective synthesis of HA is described, employing asymmetric syn-crotylation methodology to introduce the C10, C11, C14, and C15 stereocenters. The C6-C7 stereocenters were introduced using Brown's a-pinene-derived gamma-methoxy allylborane reagent. The C12 stereocenter was established by diastereoselective hydroboration.

  DOI：

  10.1021/ol036092p
• 作为产物：
  描述：

  tert-butyl-[(2R,3S,5S,6R)-6-(2,5-dimethoxy-3-nitrophenyl)-3,6-dimethoxy-5-methyl-2-phenylmethoxyhexoxy]-dimethylsilane 在 三氟甲磺酸三甲基硅酯 、 三氯化硼-甲硫醚 、 四丁基氟化铵 作用下， 生成 methyl (E,5S,6R,7S,9S,10R)-10-(2,5-dimethoxy-3-nitrophenyl)-6,7,10-trimethoxy-5,9-dimethyldec-3-enoate
  参考文献：
  名称：

  Total Synthesis of Herbimycin A

  摘要：

  Herbimycin A (HA) belongs to a class of antibiotics known as the benzoquinoid ansamycins. Members of this class have shown promising biological activity as Hsp90 inhibitors. An enantioselective synthesis of HA is described, employing asymmetric syn-crotylation methodology to introduce the C10, C11, C14, and C15 stereocenters. The C6-C7 stereocenters were introduced using Brown's a-pinene-derived gamma-methoxy allylborane reagent. The C12 stereocenter was established by diastereoselective hydroboration.

  DOI：

  10.1021/ol036092p

文献信息

• Chiral Crotylsilane-Based Approach to Benzoquinoid Ansamycins:  Total Synthesis of (+)-Macbecin I
  作者：James S. Panek、Feng Xu、Ana C. Rondón

  DOI：10.1021/ja974318b

  日期：1998.5.1

  A highly convergent total synthesis of the antitumor antibiotic (+)-macbecin I (1) has been achieved through the homologation of the aldehyde 3 (C5−C21 aromatic fragment) to the E,Z-dienoate 2 by employing a sequential olefination strategy. Subsequent macrolactonization and a final two-step oxidation sequence were the principle steps used to complete the synthesis. Six of the seven syn-stereochemical

  通过采用顺序烯化策略将醛 3（C5-C21 芳族片段）与 E,Z-二烯酸酯 2 同源，实现了抗肿瘤抗生素 (+)-macbecin I (1) 的高度收敛全合成。随后的大环内酯化和最终的两步氧化序列是用于完成合成的主要步骤。使用我们的不对称巴豆化键构建方法引入了七个合成立体化学关系中的六个（C6-C7、C10-C11 和 C14-C15）。C12 立体中心是通过烷氧基导向的硼氢化反应引入的。通过 1,1-二取代烯烃 6b 的非对映选择性硼氢化反应引入 C10 立体中心的替代策略为中间体 7 提供了一种原子效率更高的方法。
• Total Synthesis of Herbimycin A
  作者：Kendra D. Carter、James S. Panek

  DOI：10.1021/ol036092p

  日期：2004.1.1

  Herbimycin A (HA) belongs to a class of antibiotics known as the benzoquinoid ansamycins. Members of this class have shown promising biological activity as Hsp90 inhibitors. An enantioselective synthesis of HA is described, employing asymmetric syn-crotylation methodology to introduce the C10, C11, C14, and C15 stereocenters. The C6-C7 stereocenters were introduced using Brown's a-pinene-derived gamma-methoxy allylborane reagent. The C12 stereocenter was established by diastereoselective hydroboration.