(1R,3S,5S,7R,8R,10S,11S,12R,16R,19S,20S,21S,22R,23S,24S,30S,33S,36S,38R)-7,21,22,24-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-8-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-11,38-dimethyl-32,39-dimethylidene-4,9,13,40,41,42,43-heptaoxaheptacyclo[34.3.1.116,20.119,23.130,33.03,12.05,10]tritetracont-25-yne-14,27-dione | 1353268-82-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (1R,3S,5S,7R,8R,10S,11S,12R,16R,19S,20S,21S,22R,23S,24S,30S,33S,36S,38R)-7,21,22,24-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-8-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-11,38-dimethyl-32,39-dimethylidene-4,9,13,40,41,42,43-heptaoxaheptacyclo[34.3.1.116,20.119,23.130,33.03,12.05,10]tritetracont-25-yne-14,27-dione
• CAS: 1353268-82-2
• 化学式: C₇₂H₁₃₀O₁₄Si₅
• 分子量: 1360.24
• InChiKey: CAHKEFDIDNQGGB-FJMBVRBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.74
• 重原子数：
  91
• 可旋转键数：
  17
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (1R,3S,5S,7R,8R,10S,11S,12R,16R,19S,20S,21S,22R,23S,24S,30S,33S,36S,38R)-7,21,22,24-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-8-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-11,38-dimethyl-32,39-dimethylidene-4,9,13,40,41,42,43-heptaoxaheptacyclo[34.3.1.116,20.119,23.130,33.03,12.05,10]tritetracont-25-yne-14,27-dione 在 1H-imidazole hydrochloride 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Total Synthesis of Halichondrin C

  摘要：

  The first total synthesis of halichondrin C has been completed, highlighted by development of the synthetic method to construct the C8-C14 polycycle. Cr-mediated coupling reactions are used seven times to form a new C C bond. The acid stability of halichondrin C is studied, demonstrating that the macrolactone stabilizes the C8-C14 polycycle, relative to the one present in the C1-C16 model.

  DOI：

  10.1021/ja2108307
• 作为产物：
  描述：

  2-[(2S,3R,4S,4aS,6R,8aS)-2-[(1S)-6-[(2S,5S)-5-[2-[(2S,4R,6R)-6-[[(2S,3R,4R,4aS,6R,7R,8aS)-7-[tert-butyl(dimethyl)silyl]oxy-6-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-3-hydroxy-4-methyl-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]methyl]-4-methyl-5-methylideneoxan-2-yl]ethyl]-4-methylideneoxolan-2-yl]-1-[tert-butyl(dimethyl)silyl]oxy-4-oxohex-2-ynyl]-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-6-yl]acetic acid 在 4-二甲氨基吡啶 、 2-甲基-6-硝基苯甲酸酐 作用下， 以 甲苯 为溶剂， 反应 6.25h， 以93%的产率得到(1R,3S,5S,7R,8R,10S,11S,12R,16R,19S,20S,21S,22R,23S,24S,30S,33S,36S,38R)-7,21,22,24-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-8-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-11,38-dimethyl-32,39-dimethylidene-4,9,13,40,41,42,43-heptaoxaheptacyclo[34.3.1.116,20.119,23.130,33.03,12.05,10]tritetracont-25-yne-14,27-dione
  参考文献：
  名称：

  Total Synthesis of Halichondrin C

  摘要：

  The first total synthesis of halichondrin C has been completed, highlighted by development of the synthetic method to construct the C8-C14 polycycle. Cr-mediated coupling reactions are used seven times to form a new C C bond. The acid stability of halichondrin C is studied, demonstrating that the macrolactone stabilizes the C8-C14 polycycle, relative to the one present in the C1-C16 model.

  DOI：

  10.1021/ja2108307

文献信息

• Total Synthesis of Halichondrin C
  作者：Akihiko Yamamoto、Atsushi Ueda、Paul Brémond、Paolo S. Tiseni、Yoshito Kishi

  DOI：10.1021/ja2108307

  日期：2012.1.18

  The first total synthesis of halichondrin C has been completed, highlighted by development of the synthetic method to construct the C8-C14 polycycle. Cr-mediated coupling reactions are used seven times to form a new C C bond. The acid stability of halichondrin C is studied, demonstrating that the macrolactone stabilizes the C8-C14 polycycle, relative to the one present in the C1-C16 model.