methyl (3E,3aR,6S,7R,7aR)-3-[(2E,4S,5S,6E)-8-[(2R,3S,6S,8R,10S)-2-[(2S)-butan-2-yl]-10-[tert-butyl(dimethyl)silyl]oxy-3-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-4,6-dimethyl-5-(2-trimethylsilylethoxymethoxy)octa-2,6-dienylidene]-3a-hydroxy-6-methyl-7-(2-trimethylsilylethoxymethoxy)-7,7a-dihydro-6H-1-benzofuran-4-carboxylate | 163452-27-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3E,3aR,6S,7R,7aR)-3-[(2E,4S,5S,6E)-8-[(2R,3S,6S,8R,10S)-2-[(2S)-butan-2-yl]-10-[tert-butyl(dimethyl)silyl]oxy-3-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-4,6-dimethyl-5-(2-trimethylsilylethoxymethoxy)octa-2,6-dienylidene]-3a-hydroxy-6-methyl-7-(2-trimethylsilylethoxymethoxy)-7,7a-dihydro-6H-1-benzofuran-4-carboxylate
• CAS: 163452-27-5
• 化学式: C₅₃H₉₄O₁₁Si₃
• 分子量: 991.579
• InChiKey: AMAJZSSLMBACTF-GSKLHQKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.62
• 重原子数：
  67
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (3E,3aR,6S,7R,7aR)-3-[(2E,4S,5S,6E)-8-[(2R,3S,6S,8R,10S)-2-[(2S)-butan-2-yl]-10-[tert-butyl(dimethyl)silyl]oxy-3-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-4,6-dimethyl-5-(2-trimethylsilylethoxymethoxy)octa-2,6-dienylidene]-3a-hydroxy-6-methyl-7-(2-trimethylsilylethoxymethoxy)-7,7a-dihydro-6H-1-benzofuran-4-carboxylate 在 sodium tetrahydroborate 、 disodium hydrogenphosphate 、 N-氯代丁二酰亚胺 、 正丁基锂 、 草酰氯 、 sodium methylate 、 二异丁基氢化铝 、 臭氧 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 53.5h， 生成
  参考文献：
  名称：

  Total Synthesis of the Antiparasitic Agent Avermectin B1a

  摘要：

  The synthesis of avermectin B-1a has been completed by a route that assembles the aglycon from three subunits consisting of the hexahydrobenzofuran moiety (A), the spiroketal segment (B), and the acyclic portion (C) comprising C9-C15. Connection is made in a B + C --> (B - C) + A sequence, and the synthesis is concluded by attachment to the aglycon of the L-oleandrosyl-L-oleandrose disaccharide via the pyridylthio glycoside.

  DOI：

  10.1021/ja00112a006
• 作为产物：
  描述：

  methyl (3aR,6S,7R,7aR,E)-3-((2E,4S,5S,6E)-8-((2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-hydroxy-9-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-5-hydroxy-4,6-dimethylocta-2,6-dien-1-ylidene)-3a,7-dihydroxy-6-methyl-2,3,3a,6,7,7a-hexahydrobenzofuran-4-carboxylate 在 咪唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 methyl (3E,3aR,6S,7R,7aR)-3-[(2E,4S,5S,6E)-8-[(2R,3S,6S,8R,10S)-2-[(2S)-butan-2-yl]-10-[tert-butyl(dimethyl)silyl]oxy-3-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-4,6-dimethyl-5-(2-trimethylsilylethoxymethoxy)octa-2,6-dienylidene]-3a-hydroxy-6-methyl-7-(2-trimethylsilylethoxymethoxy)-7,7a-dihydro-6H-1-benzofuran-4-carboxylate
  参考文献：
  名称：

  Total Synthesis of the Antiparasitic Agent Avermectin B1a

  摘要：

  The synthesis of avermectin B-1a has been completed by a route that assembles the aglycon from three subunits consisting of the hexahydrobenzofuran moiety (A), the spiroketal segment (B), and the acyclic portion (C) comprising C9-C15. Connection is made in a B + C --> (B - C) + A sequence, and the synthesis is concluded by attachment to the aglycon of the L-oleandrosyl-L-oleandrose disaccharide via the pyridylthio glycoside.

  DOI：

  10.1021/ja00112a006