25-cyclohexyl-5-O-demethyl-5-O-[(1,1-dimethylethyl)dimethylsilyl]-25-de(1-methylpropyl)-22,23-dihydro-avermectin A1a monosaccharide | 165108-45-2

• 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: 25-cyclohexyl-5-O-demethyl-5-O-[(1,1-dimethylethyl)dimethylsilyl]-25-de(1-methylpropyl)-22,23-dihydro-avermectin A1a monosaccharide
• 英文别名: 25-cyclohexyl-5-O-demethyl-5-O-[(1,1-dimethylethyl)dimethylsilyl]-25-de(1-methylpropyl)-22,23-dihydro-avermectin A_1a monosaccharide
• CAS: 165108-45-2
• 化学式: C₄₉H₇₈O₁₁Si
• 分子量: 871.237
• InChiKey: GYHNZMZYXPQVQP-XIMGOKSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.63
• 重原子数：
  61.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  131.37
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  25-cyclohexyl-5-O-demethyl-5-O-[(1,1-dimethylethyl)dimethylsilyl]-25-de(1-methylpropyl)-22,23-dihydro-avermectin A1a monosaccharide 在 吡啶 、 manganese(IV) oxide 、 偶氮二异丁腈 、 三正丁基氢锡 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 30.75h， 生成 25-cyclohexyl-5-demethoxy-25-de(1-methylpropyl)-4''-deoxy-22,23-dihydro-5-hydroxyimino-avermectin A_1a monosaccharide
  参考文献：
  名称：

  Avermectins and flea control: structure–activity relationships and the selection of selamectin for development as an endectocide for companion animals

  摘要：

  Evaluation of a wide range of avermectin derivatives for flea activity in an in vitro feeding screen using the cat flea, Ctenocephalides felis, revealed a narrow structure-activity relationship (SAR) with activity surprisingly associated with monosaccharides and especially their C-5-oximes. We discovered commercially exploitable flea activity in a single compound, selamectin 33, which also possessed the necessary antiparasitic spectrum and margin of safety for development as a broad-spectrum companion animal endectocide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00120-6
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (1R,4S,5'S,6R,6'S,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-cyclohexyl-21,24-dihydroxy-12-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以60%的产率得到25-cyclohexyl-5-O-demethyl-5-O-[(1,1-dimethylethyl)dimethylsilyl]-25-de(1-methylpropyl)-22,23-dihydro-avermectin A1a monosaccharide
  参考文献：
  名称：

  Avermectins and flea control: structure–activity relationships and the selection of selamectin for development as an endectocide for companion animals

  摘要：

  Evaluation of a wide range of avermectin derivatives for flea activity in an in vitro feeding screen using the cat flea, Ctenocephalides felis, revealed a narrow structure-activity relationship (SAR) with activity surprisingly associated with monosaccharides and especially their C-5-oximes. We discovered commercially exploitable flea activity in a single compound, selamectin 33, which also possessed the necessary antiparasitic spectrum and margin of safety for development as a broad-spectrum companion animal endectocide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00120-6