(3aS,5R,7aS)-5-[(1E,6S)-6-(4-methoxybenzyloxy)-1-heptenyl]hexahydrofuro[3,2-b]pyran-2-one | 1204616-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (3aS,5R,7aS)-5-[(1E,6S)-6-(4-methoxybenzyloxy)-1-heptenyl]hexahydrofuro[3,2-b]pyran-2-one
• 英文别名: (3aS,5R,7aS)-5-[(E,6S)-6-[(4-methoxyphenyl)methoxy]hept-1-enyl]-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyran-2-one
• CAS: 1204616-82-9
• 化学式: C₂₂H₃₀O₅
• 分子量: 374.477
• InChiKey: NKPCXCBVJFAKJW-GEJWFTEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,5R,7aS)-5-[(1E,6S)-6-(4-methoxybenzyloxy)-1-heptenyl]hexahydrofuro[3,2-b]pyran-2-one 在 甲醇 、 sodium chlorite 、 sodium dihydrogenphosphate 、 lithium aluminium tetrahydride 、 2-甲基-2-丁烯 、 2,4,6-三氯苯甲酰氯 、 camphor-10-sulfonic acid 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 D-脯氨酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 33.0h， 生成 (1R,5S,11R,14S,E)-14-(tert-butyldimethylsilyloxy)-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one
  参考文献：
  名称：

  Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran

  摘要：

  The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2-acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.061
• 作为产物：
  描述：

  在 三乙基硼 、 氧气 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成 (3aS,5R,7aS)-5-[(1E,6S)-6-(4-methoxybenzyloxy)-1-heptenyl]hexahydrofuro[3,2-b]pyran-2-one
  参考文献：
  名称：

  Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran

  摘要：

  The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2-acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.061

文献信息

• Synthesis of aspergillide A from a synthetic intermediate of aspergillide B
  作者：Tomohiro Nagasawa、Shigefumi Kuwahara

  DOI：10.1016/j.tetlet.2009.12.032

  日期：2010.2

  The first synthesis of aspergillide A, a cytotoxin produced by a marine-derived fungus, has been achieved from a synthetic intermediate of aspergillide B by using a proline-mediated epimerization of a 2,6-trans-substituted tetrahydropyran-2-acetaldehyde intermediate into the corresponding cis-isomer via a retro-oxy-Michael/oxy-Michael sequence as the key transformation.

  曲霉内酯A的第一次合成是由海洋真菌产生的细胞毒素，它是由曲霉内酯B的合成中间体通过脯氨酸介导的2，6-反式取代的四氢吡喃-2-乙醛中间体差向异构化成相应的顺式异构体通过反-氧-迈克尔/氧-迈克尔序列作为关键转化。
• Enantioselective Synthesis of Aspergillide B
  作者：Tomohiro NAGASAWA、Shigefumi KUWAHARA

  DOI：10.1271/bbb.90221

  日期：2009.8.23

  The enantioselective synthesis of aspergillide B, a 14-membered macrocyclic cytotoxin, was achieved in a 49% yield via 7 steps from a synthetic intermediate of aspergillide C. The spectroscopic data and specific rotation value for the synthetic material matched those of natural aspergillide B.

  由曲霉内酯C的合成中间体经过7个步骤，以49％的产率实现了对映体选择性合成14元大环细胞毒素的曲霉内酯B.合成材料的光谱数据和比旋光度与天然曲霉内酯B的光谱数据和比旋光度匹配。
• Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran
  作者：Tomohiro Nagasawa、Tomoo Nukada、Shigefumi Kuwahara

  DOI：10.1016/j.tet.2011.02.061

  日期：2011.4

  The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2-acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps. (C) 2011 Elsevier Ltd. All rights reserved.