methyl (3aα,4β,6α,7β,7aα)-octahydro-6,7-dihydroxy-6-methyl-3-oxo-4-benzofurancarboxylate | 116137-59-8

• 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,7β,7aα)-octahydro-6,7-dihydroxy-6-methyl-3-oxo-4-benzofurancarboxylate
• 英文别名: methyl (3aS,4S,6S,7S,7aS)-6,7-dihydroxy-6-methyl-3-oxo-4,5,7,7a-tetrahydro-3aH-1-benzofuran-4-carboxylate
• CAS: 116137-59-8
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: HLJHTZAECKZFIJ-KHWWSFOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.12
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (3aα,4β,6α,7β,7aα)-octahydro-6,7-dihydroxy-6-methyl-3-oxo-4-benzofurancarboxylate 在 吡啶 、 4-二甲氨基吡啶 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 methyl (3aα,4β,7β,7aα)-7-(acetyloxy)-octahydro-6-methylene-3-oxo-4-benzofuranocarboxylate
  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 N-溴代丁二酰亚胺(NBS) 、 高氯酸 、 草酰氯 、 2,6-二叔丁基-4-甲基苯酚 、 硫酸 、 四丁基氟化铵 、 水 、 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 、 水 、 丙酮 、 苯 为溶剂， 反应 27.92h， 生成 methyl (3aα,4β,6α,7β,7aα)-octahydro-6,7-dihydroxy-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

• WHITE, JAMES D.;DANTANARAYANA, ANURA P., TETRAHEDRON LETT., 28,(1987) N 51, 6417-6420
  作者：WHITE, JAMES D.、DANTANARAYANA, ANURA P.

  DOI：——

  日期：——
• 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.