22,23-dihydro-5-O-tert-butydimethylsilyl-7,13-O-bis-trimethylsilyl-avermectin B1 aglycon | 150807-30-0

• 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: 22,23-dihydro-5-O-tert-butydimethylsilyl-7,13-O-bis-trimethylsilyl-avermectin B1 aglycon
• 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-[tert-butyl(dimethyl)silyl]oxy-5',11,13,22-tetramethyl-12,24-bis(trimethylsilyloxy)spiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one
• CAS: 150807-30-0
• 化学式: C₄₆H₈₀O₈Si₃
• 分子量: 845.393
• InChiKey: XVWOPWVYBBZFEU-GXJBBSHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.28
• 重原子数：
  57.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  22,23-dihydro-5-O-tert-butydimethylsilyl-7,13-O-bis-trimethylsilyl-avermectin B1 aglycon 在 咪唑 、 titanium(IV) isopropylate 、 盐酸 、 二氯乙酸 、 4-二甲氨基吡啶 、 三甲基氯硅烷 、 18-冠醚-6 、 水 、 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 110.67h， 生成 13β-O-methoxymethyl-22,23-dihydroavermectin B1 aglycon
  参考文献：
  名称：

  Practical Syntheses of 13-O-[(2-Methoxyethoxy)methyl]-22,23-dihydroavermectin B₁ Aglycon [Dimedectin Isopropanol, MK-324] and 13-epi-O-(Methoxymethyl)-22,23-dihydroavermectin B₁ Aglycon [L-694,554], Flea Active Ivermectin Analogues

  摘要：

  Practical high yielding syntheses of 13-O-[(2-methoxyethoxy)methyl]-22,23-dihydroavermectin B-1 aglycon (dimedectin 2-propanol, MK-324, 1) and 13-epi-O-(methoxymethyl)-22,23-dihydroavermectin B-1 aglycon (L-694,554, 2), both potent flea insecticides, from ivermectin are presented. The successful selective manipulation of silyl protecting groups on ivermectin aglycon led to the facile preparation of 5,7-O-bis-silyl-22,23-dihydroavermectin B-1 aglycon 7 as the key intermediate for the large scale syntheses of these compounds. Development of a dual pyridine/tertiary amine system for mesylation of the C-13 alpha hydroxyl group of 7 and subsequent displacement with cesium propionate-propionic acid led to the successful inversion of the 13-hydroxy group.

  DOI：

  10.1021/jo970187l
• 作为产物：
  描述：

  ivermectin aglycone 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 22,23-dihydro-5-O-tert-butydimethylsilyl-7,13-O-bis-trimethylsilyl-avermectin B1 aglycon
  参考文献：
  名称：

  Practical Syntheses of 13-O-[(2-Methoxyethoxy)methyl]-22,23-dihydroavermectin B₁ Aglycon [Dimedectin Isopropanol, MK-324] and 13-epi-O-(Methoxymethyl)-22,23-dihydroavermectin B₁ Aglycon [L-694,554], Flea Active Ivermectin Analogues

  摘要：

  Practical high yielding syntheses of 13-O-[(2-methoxyethoxy)methyl]-22,23-dihydroavermectin B-1 aglycon (dimedectin 2-propanol, MK-324, 1) and 13-epi-O-(methoxymethyl)-22,23-dihydroavermectin B-1 aglycon (L-694,554, 2), both potent flea insecticides, from ivermectin are presented. The successful selective manipulation of silyl protecting groups on ivermectin aglycon led to the facile preparation of 5,7-O-bis-silyl-22,23-dihydroavermectin B-1 aglycon 7 as the key intermediate for the large scale syntheses of these compounds. Development of a dual pyridine/tertiary amine system for mesylation of the C-13 alpha hydroxyl group of 7 and subsequent displacement with cesium propionate-propionic acid led to the successful inversion of the 13-hydroxy group.

  DOI：

  10.1021/jo970187l