22,23-Dihydro-5-O-demethyl-26-((2-methoxyethoxy)methoxy)avermectin A1a | 156153-56-9

• 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: 22,23-Dihydro-5-O-demethyl-26-((2-methoxyethoxy)methoxy)avermectin A1a
• 英文别名: (1R,4S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-[(2S)-butan-2-yl]-21,24-dihydroxy-12-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-22-(2-methoxyethoxymethoxymethyl)-5',11,13-trimethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one
• CAS: 156153-56-9
• 化学式: C₅₂H₈₂O₁₇
• 分子量: 979.213
• InChiKey: LRCJTKFGIGIPAE-WVCPODIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  69
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  198
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  (1R,4S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-[(2S)-butan-2-yl]-21,24-dihydroxy-12-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-22-(hydroxymethyl)-5',11,13-trimethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one 在 吡啶 、 咪唑 、 氢氟酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 22,23-Dihydro-5-O-demethyl-26-((2-methoxyethoxy)methoxy)avermectin A1a
  参考文献：
  名称：

  Synthesis and Biological Activity of 4a,4"-Disubstituted Avermectins

  摘要：

  Allylic oxidation of avermectin B-1 and C-4''-substituted avermectin B-1 analogues at C-4a followed by derivatization of the C-4a oxygen provides compounds that have an improved safety profile, as judged by mouse LD(50) data, and are substantially more potent than avermectin B-1 against flies.

  DOI：

  10.1021/jf00044a041

文献信息

• Synthesis and Biological Activity of 4a,4"-Disubstituted Avermectins
  作者：Todd K. Jones、Lin Chu、Helmut Mrozik、Lyndia Slayton、Bryan Rafalko、Mary Lee Goldmann、Wesley L. Shoop、Gaye Margiatto、Michael H. Fisher

  DOI：10.1021/jf00044a041

  日期：1994.8

  Allylic oxidation of avermectin B-1 and C-4''-substituted avermectin B-1 analogues at C-4a followed by derivatization of the C-4a oxygen provides compounds that have an improved safety profile, as judged by mouse LD(50) data, and are substantially more potent than avermectin B-1 against flies.