2-[(1S,3R,6S,9S,12S,14R,16R,18S,20S,22R,23R,25S,26S,27R,31R,34S,36R,37R,38R,40R,41S)-22-[tert-butyl(dimethyl)silyl]oxy-14,26-dimethyl-8,15-dimethylidene-29-oxo-38-prop-2-enoxy-2,19,24,28,35,39,42,44,45,46-decaoxadecacyclo[29.9.2.13,37.13,38.16,9.112,16.018,27.020,25.034,41.036,40]hexatetracontan-23-yl]acetaldehyde | 1353268-98-0

• 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: 2-[(1S,3R,6S,9S,12S,14R,16R,18S,20S,22R,23R,25S,26S,27R,31R,34S,36R,37R,38R,40R,41S)-22-[tert-butyl(dimethyl)silyl]oxy-14,26-dimethyl-8,15-dimethylidene-29-oxo-38-prop-2-enoxy-2,19,24,28,35,39,42,44,45,46-decaoxadecacyclo[29.9.2.13,37.13,38.16,9.112,16.018,27.020,25.034,41.036,40]hexatetracontan-23-yl]acetaldehyde
• CAS: 1353268-98-0
• 化学式: C₅₁H₇₆O₁₄Si
• 分子量: 941.242
• InChiKey: PCPYAAOVNQUGML-PXDUZTSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.35
• 重原子数：
  66
• 可旋转键数：
  8
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  、 2-[(1S,3R,6S,9S,12S,14R,16R,18S,20S,22R,23R,25S,26S,27R,31R,34S,36R,37R,38R,40R,41S)-22-[tert-butyl(dimethyl)silyl]oxy-14,26-dimethyl-8,15-dimethylidene-29-oxo-38-prop-2-enoxy-2,19,24,28,35,39,42,44,45,46-decaoxadecacyclo[29.9.2.13,37.13,38.16,9.112,16.018,27.020,25.034,41.036,40]hexatetracontan-23-yl]acetaldehyde 在 chromium dichloride 、 (S)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methoxyphenyl)methanesulfonamide 、 NiCl₂*2,9-diethyl-1,10-phenanthroline complex 、 1,8-双二甲氨基萘 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 0.75h， 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：

  在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到2-[(1S,3R,6S,9S,12S,14R,16R,18S,20S,22R,23R,25S,26S,27R,31R,34S,36R,37R,38R,40R,41S)-22-[tert-butyl(dimethyl)silyl]oxy-14,26-dimethyl-8,15-dimethylidene-29-oxo-38-prop-2-enoxy-2,19,24,28,35,39,42,44,45,46-decaoxadecacyclo[29.9.2.13,37.13,38.16,9.112,16.018,27.020,25.034,41.036,40]hexatetracontan-23-yl]acetaldehyde
  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.