2-[(2R,3R,6S)-6-[(E,6S)-6-hydroxyhept-1-enyl]-3-(methoxymethoxy)oxan-2-yl]acetic acid | 1164113-65-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-[(2R,3R,6S)-6-[(E,6S)-6-hydroxyhept-1-enyl]-3-(methoxymethoxy)oxan-2-yl]acetic acid
• CAS: 1164113-65-8
• 化学式: C₁₆H₂₈O₆
• 分子量: 316.395
• InChiKey: CEPVEYGHNWTSQJ-RTCUBQDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(2R,3R,6S)-6-[(E,6S)-6-hydroxyhept-1-enyl]-3-(methoxymethoxy)oxan-2-yl]acetic acid 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 5.0h， 以65%的产率得到(1R,5R,9E,11S,14R)-14-(methoxymethoxy)-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one
  参考文献：
  名称：

  Concise Total Synthesis of (+)-Aspergillide B

  摘要：

  An efficient total synthesis of (+)-aspergillide B has been achieved, which features the C-glycosylation reaction for constructing the 2,6-trans-substituted pyran core, a highly effective four-step sequence without purification to produce the key intermediate 13 and an advantegous E-selective Julia-Kocienski olefination on a highly elaborate substrate. The synthesis confirmed the revised structure of aspergillide B by Uenishi.

  DOI：

  10.1021/jo900820f
• 作为产物：
  描述：

  在 lithium hydroxide 、 水 、 柠檬酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 2-[(2R,3R,6S)-6-[(E,6S)-6-hydroxyhept-1-enyl]-3-(methoxymethoxy)oxan-2-yl]acetic acid
  参考文献：
  名称：

  Concise Total Synthesis of (+)-Aspergillide B

  摘要：

  An efficient total synthesis of (+)-aspergillide B has been achieved, which features the C-glycosylation reaction for constructing the 2,6-trans-substituted pyran core, a highly effective four-step sequence without purification to produce the key intermediate 13 and an advantegous E-selective Julia-Kocienski olefination on a highly elaborate substrate. The synthesis confirmed the revised structure of aspergillide B by Uenishi.

  DOI：

  10.1021/jo900820f

文献信息

• Concise Total Synthesis of (+)-Aspergillide B
  作者：Jian Liu、Ke Xu、Jinmei He、Ling Zhang、Xinfu Pan、Xuegong She

  DOI：10.1021/jo900820f

  日期：2009.7.17

  An efficient total synthesis of (+)-aspergillide B has been achieved, which features the C-glycosylation reaction for constructing the 2,6-trans-substituted pyran core, a highly effective four-step sequence without purification to produce the key intermediate 13 and an advantegous E-selective Julia-Kocienski olefination on a highly elaborate substrate. The synthesis confirmed the revised structure of aspergillide B by Uenishi.