methyl (3aα,4β,6α,7aα)-7-(acetyloxy)octahydro-6-iodo-6-methyl-3-oxo-4-benzofurancarboxylate | 163452-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: methyl (3aα,4β,6α,7aα)-7-(acetyloxy)octahydro-6-iodo-6-methyl-3-oxo-4-benzofurancarboxylate
• CAS: 163452-15-1
• 化学式: C₁₃H₁₇IO₆
• 分子量: 396.179
• InChiKey: AQTFGNUEVRXTDK-NTGGNFCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (3aα,4β,6α,7aα)-7-(acetyloxy)octahydro-6-iodo-6-methyl-3-oxo-4-benzofurancarboxylate 在 2,6-二甲基吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.5h， 生成 methyl (3aα,4β,6α,7β,7aα)-7-(acetyloxy)octahydro-3a-hydroxy-6-iodo-6-methyl-3-oxo-4-benzofurancarboxylate
  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：

  (E)-trimethyl((3-methylbuta-1,3-dien-1-yl)oxy)silane 在 吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 草酰氯 、 2,6-二叔丁基-4-甲基苯酚 、 硫酸 、 四丁基氟化铵 、 水 、 氢碘酸 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 18.92h， 生成 methyl (3aα,4β,6α,7aα)-7-(acetyloxy)octahydro-6-iodo-6-methyl-3-oxo-4-benzofurancarboxylate
  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

文献信息

• Total Synthesis of the Antiparasitic Agent Avermectin B1a
  作者：James D. White、Gary L. Bolton、Anura P. Dantanarayana、Christina M. J. Fox、Roger N. Hiner、Randy W. Jackson、Kazuhiko Sakuma、Ulhas S. Warrier

  DOI：10.1021/ja00112a006

  日期：1995.2

  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.