dolabelide D | 185843-01-0

• 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: dolabelide D
• 英文别名: [(3S,4S,5R,8S,10R,12S,15E,20R,22S,23S,24R)-24-[(E,4R)-4-acetyloxy-2-methylhept-1-enyl]-4,8,12,20,22-pentahydroxy-3,5,15,23-tetramethyl-2-oxo-1-oxacyclotetracos-15-en-10-yl] acetate
• CAS: 185843-01-0
• 化学式: C₃₉H₆₈O₁₁
• 分子量: 712.962
• InChiKey: VJFQDPJVPBUKKD-QFWAPRMHSA-N

物化性质

• 沸点：
  813.2±65.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  50
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  180
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 dolabelide D 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 3.0h， 以89%的产率得到Acetic acid (E)-(2R,3S,4S,6R,14S,16R,18S,21R,22S,23S)-6,14,16,18,22-pentaacetoxy-2-((E)-(R)-4-acetoxy-2-methyl-hept-1-enyl)-3,11,21,23-tetramethyl-24-oxo-oxacyclotetracos-10-en-4-yl ester
  参考文献：
  名称：

  Dolabelides C and D, Cytotoxic Macrolides Isolated from the Sea Hare Dolabella auricularia

  摘要：

  Two new cytotoxic 24-membered macrolides, dolabelides C and D, were isolated from the Japanese sea hare Dolabella auricularia. Their gross structures were deduced by spectroscopic analysis including the 2D NMR technique, and their absolute stereochemistry was determined by means of chemical correlation with the known dolabelide A. Dolabelides C and D exhibited cytotoxicities against HeLa S-3 cells with IC50 values of 1.9 and 1.5 mu g/mL, respectively.

  DOI：

  10.1021/np960612q
• 作为产物：
  描述：

  5-己烯醛 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 三乙胺 、 (+)-二异松蒎基氯硼烷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 、 乙醚 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 138.67h， 生成 dolabelide D
  参考文献：
  名称：

  Total Synthesis of Dolabelide D

  摘要：

  The first total synthesis of dolabelide D (or of any of the closely related dolabelides) has been achieved with a longest linear sequence of 17 steps. Key features of the synthesis include an application of the catalytic asymmetric silane alcoholysis, the tandem silylformylation-crotylsilylation, and a Brook-like 1,4-carbon to oxygen silyl migration.

  DOI：

  10.1021/ja058692k

文献信息

• Total Synthesis of Dolabelide D
  作者：Peter K. Park、Steven J. O'Malley、Darby R. Schmidt、James L. Leighton

  DOI：10.1021/ja058692k

  日期：2006.3.1

  The first total synthesis of dolabelide D (or of any of the closely related dolabelides) has been achieved with a longest linear sequence of 17 steps. Key features of the synthesis include an application of the catalytic asymmetric silane alcoholysis, the tandem silylformylation-crotylsilylation, and a Brook-like 1,4-carbon to oxygen silyl migration.
• Dolabelides C and D, Cytotoxic Macrolides Isolated from the Sea Hare <i>Dolabella auricularia</i>
  作者：Kiyotake Suenaga、Tomohiro Nagoya、Takunobu Shibata、Hideo Kigoshi、Kiyoyuki Yamada

  DOI：10.1021/np960612q

  日期：1997.2.1

  Two new cytotoxic 24-membered macrolides, dolabelides C and D, were isolated from the Japanese sea hare Dolabella auricularia. Their gross structures were deduced by spectroscopic analysis including the 2D NMR technique, and their absolute stereochemistry was determined by means of chemical correlation with the known dolabelide A. Dolabelides C and D exhibited cytotoxicities against HeLa S-3 cells with IC50 values of 1.9 and 1.5 mu g/mL, respectively.