methyl (2S,4Z)-2-[[(3aS,8bR)-8b-[tert-butyl(dimethyl)silyl]oxy-2,3a-dihydro-1H-furo[2,3-b]indol-4-yl]methyl]-4-ethylidene-2-methyl-3-oxo-5-trimethylsilyloctanoate | 405297-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl (2S,4Z)-2-[[(3aS,8bR)-8b-[tert-butyl(dimethyl)silyl]oxy-2,3a-dihydro-1H-furo[2,3-b]indol-4-yl]methyl]-4-ethylidene-2-methyl-3-oxo-5-trimethylsilyloctanoate
• CAS: 405297-79-2
• 化学式: C₃₂H₅₃NO₅Si₂
• 分子量: 587.948
• InChiKey: JMEBKOZYGZOPDJ-HPUYKRRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,4Z)-2-[[(3aS,8bR)-8b-[tert-butyl(dimethyl)silyl]oxy-2,3a-dihydro-1H-furo[2,3-b]indol-4-yl]methyl]-4-ethylidene-2-methyl-3-oxo-5-trimethylsilyloctanoate 在 四丁基二氟三苯硅酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 以52%的产率得到(+)-madindoline A
  参考文献：
  名称：

  Short Total Synthesis of (+)-Madindolines A and B

  摘要：

  A short and efficient total synthesis of (+)-madindolines A (1) and B (2), potent and selective inhibitors of interleukin 6, has been achieved. The synthesis features a key chelation-controlled 1,4-diastereoselective acylation to generate the quaternary carbon and an intramolecular acylation of allylsilane to build up the cyclopentene unit.

  DOI：

  10.1021/ol017058i
• 作为产物：
  描述：

  [(2S),3aR,8aS]-3a-(tert-butyldimethylsilyloxy)-8-(2-carboxypropyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 苯 为溶剂， 反应 2.6h， 生成 methyl (2S,4Z)-2-[[(3aS,8bR)-8b-[tert-butyl(dimethyl)silyl]oxy-2,3a-dihydro-1H-furo[2,3-b]indol-4-yl]methyl]-4-ethylidene-2-methyl-3-oxo-5-trimethylsilyloctanoate
  参考文献：
  名称：

  Short Total Synthesis of (+)-Madindolines A and B

  摘要：

  A short and efficient total synthesis of (+)-madindolines A (1) and B (2), potent and selective inhibitors of interleukin 6, has been achieved. The synthesis features a key chelation-controlled 1,4-diastereoselective acylation to generate the quaternary carbon and an intramolecular acylation of allylsilane to build up the cyclopentene unit.

  DOI：

  10.1021/ol017058i

文献信息

• Short Total Synthesis of (+)-Madindolines A and B
  作者：Tomoyasu Hirose、Toshiaki Sunazuka、Tatsuya Shirahata、Daisuke Yamamoto、Yoshihiro Harigaya、Isao Kuwajima、Satoshi Ōmura

  DOI：10.1021/ol017058i

  日期：2002.2.1

  A short and efficient total synthesis of (+)-madindolines A (1) and B (2), potent and selective inhibitors of interleukin 6, has been achieved. The synthesis features a key chelation-controlled 1,4-diastereoselective acylation to generate the quaternary carbon and an intramolecular acylation of allylsilane to build up the cyclopentene unit.