(3aR,6S,7R,7aR)-3a-Hydroxy-3-[2-hydroxy-eth-(E)-ylidene]-6-methyl-7-(2-trimethylsilanyl-ethoxymethoxy)-2,3,3a,6,7,7a-hexahydro-benzofuran-4-carboxylic acid methyl ester | 163452-28-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,6S,7R,7aR)-3a-Hydroxy-3-[2-hydroxy-eth-(E)-ylidene]-6-methyl-7-(2-trimethylsilanyl-ethoxymethoxy)-2,3,3a,6,7,7a-hexahydro-benzofuran-4-carboxylic acid methyl ester
• 英文别名: methyl (3E,3aR,6S,7R,7aR)-3a-hydroxy-3-(2-hydroxyethylidene)-6-methyl-7-(2-trimethylsilylethoxymethoxy)-7,7a-dihydro-6H-1-benzofuran-4-carboxylate
• CAS: 163452-28-6
• 化学式: C₁₉H₃₂O₇Si
• 分子量: 400.544
• InChiKey: CPRLUYVRIFNMFQ-YUYSUCEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,6S,7R,7aR)-3a-Hydroxy-3-[2-hydroxy-eth-(E)-ylidene]-6-methyl-7-(2-trimethylsilanyl-ethoxymethoxy)-2,3,3a,6,7,7a-hexahydro-benzofuran-4-carboxylic acid methyl ester 在 吡啶 、 disodium hydrogenphosphate 、 sodium amalgam 、 正丁基锂 、 二甲基硫 、 四丁基氟化铵 、 sodium methylate 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 26.42h， 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：

  在 sodium tetrahydroborate 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 (3aR,6S,7R,7aR)-3a-Hydroxy-3-[2-hydroxy-eth-(E)-ylidene]-6-methyl-7-(2-trimethylsilanyl-ethoxymethoxy)-2,3,3a,6,7,7a-hexahydro-benzofuran-4-carboxylic acid methyl ester
  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