20-Hydroxyecdysone-22-beta-D-glucopyranoside

• 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: 20-Hydroxyecdysone-22-beta-D-glucopyranoside
• 英文别名: 20-hydroxyecdysone 22-β-D-glucopyranoside；(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,6-dihydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• 化学式: C₃₃H₅₄O₁₂
• 分子量: 642.785
• InChiKey: OYLAWXRQIJWVHG-SQFUCQSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  218
• 氢给体数：
  9
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  蜕皮激素 在 potassium cyanide 、 Ag-silicate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 20-Hydroxyecdysone-22-beta-D-glucopyranoside
  参考文献：
  名称：

  Regioselective synthesis of 20-hydroxyecdysone glycosides

  摘要：

  Four beta-D-glucopyranosides of 20-hydroxyecdysone (1) were prepared. The regioselective course of glycosylation was achieved by the combination of hydroxyl and 1,2-diol protective groups, i.e. acetates and phenyl boronates, in the aglycone moiety.

  DOI：

  10.1016/s0040-4020(01)85536-8

文献信息

• Regioselective synthesis of 20-hydroxyecdysone glycosides
  作者：Jaroslav Píš、Jiří Hykl、Miloš Buděšinský、Juraj Harmatha

  DOI：10.1016/s0040-4020(01)85536-8

  日期：1994.1

  Four beta-D-glucopyranosides of 20-hydroxyecdysone (1) were prepared. The regioselective course of glycosylation was achieved by the combination of hydroxyl and 1,2-diol protective groups, i.e. acetates and phenyl boronates, in the aglycone moiety.