[(2S,3R,5R,9R,10R,13R,14S,17S)-14-hydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2-methylsulfonyloxy-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate | 927197-45-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [(2S,3R,5R,9R,10R,13R,14S,17S)-14-hydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2-methylsulfonyloxy-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 927197-45-3
• 化学式: C₃₃H₅₂O₁₀S
• 分子量: 640.836
• InChiKey: UNUUYSVNMUAJMO-IKLZMEIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2S,3R,5R,9R,10R,13R,14S,17S)-14-hydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2-methylsulfonyloxy-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 (3R,5R,9R,10R,13R,14S,17S)-3,14-Dihydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methyl-butyl)-2,2,4-trimethyl-[1,3]dioxolan-4-yl]-10,13-dimethyl-3,4,5,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-6-one
  参考文献：
  名称：

  Stereoselective synthesis and moulting activity of integristerone A and analogues

  摘要：

  Integristerone A, a rare ecdysteroid of plant origin, has been synthesized from 20-hydroxyecdysone with 2-deoxy- 1,2-didehydro-20-hydroxyecdysone as the key intermediate, followed by stereoselective asymmetric dihydroxylation. The analogues 1,2-di-epi-integristerone A and 1,2-di-epi-5 alpha-integristerone A have also been synthesized. Integristerone A exhibited approximately 9-fold lower moulting activity than the parent 20-hydroxyecdysone in the Musca domestica bioassay, indicating that the presence of a 1 beta-hydroxyl group resulted in a decrease in activity. As expected, the 1,2-di-epi-5 alpha-analogue was inactive in this assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.063
• 作为产物：
  描述：

  乙酸酐 、 20-hydroxyecdysone 20,22-acetonide 2-mesylate 在 吡啶 作用下， 以95%的产率得到[(2S,3R,5R,9R,10R,13R,14S,17S)-14-hydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2-methylsulfonyloxy-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
  参考文献：
  名称：

  Stereoselective synthesis and moulting activity of integristerone A and analogues

  摘要：

  Integristerone A, a rare ecdysteroid of plant origin, has been synthesized from 20-hydroxyecdysone with 2-deoxy- 1,2-didehydro-20-hydroxyecdysone as the key intermediate, followed by stereoselective asymmetric dihydroxylation. The analogues 1,2-di-epi-integristerone A and 1,2-di-epi-5 alpha-integristerone A have also been synthesized. Integristerone A exhibited approximately 9-fold lower moulting activity than the parent 20-hydroxyecdysone in the Musca domestica bioassay, indicating that the presence of a 1 beta-hydroxyl group resulted in a decrease in activity. As expected, the 1,2-di-epi-5 alpha-analogue was inactive in this assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.063