(2E,4E,6E,8S,9R,10R)-ethyl 9-methoxy-10-((4R,5S,6R)-6-((2E,4E)-6-(4-methoxybenzyloxy)-4-methylhexa-2,4-dien-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-8-methylundeca-2,4,6-trienoate | 1187629-64-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2E,4E,6E,8S,9R,10R)-ethyl 9-methoxy-10-((4R,5S,6R)-6-((2E,4E)-6-(4-methoxybenzyloxy)-4-methylhexa-2,4-dien-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-8-methylundeca-2,4,6-trienoate
• 英文别名: ethyl (2E,4E,6E,8S,9R,10R)-9-methoxy-10-[(4R,5S,6R)-6-[(2E,4E)-6-[(4-methoxyphenyl)methoxy]-4-methylhexa-2,4-dien-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]-8-methylundeca-2,4,6-trienoate
• CAS: 1187629-64-6
• 化学式: C₃₇H₅₄O₇
• 分子量: 610.832
• InChiKey: VVYPAMMHMQFXEE-VFAVQIBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2S,3R,4R)-3-methoxy-4-((4R,5S,6R)-6-((2E,4E)-6-(4-methoxybenzyloxy)-4-methylhexa-2,4-dien-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-2-methylpentanal 、 (2E,4E)-6-(diethoxyphosphoryl)hexa-2,4-dienoic acid ethyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 以71 mg的产率得到(2E,4E,6E,8S,9R,10R)-ethyl 9-methoxy-10-((4R,5S,6R)-6-((2E,4E)-6-(4-methoxybenzyloxy)-4-methylhexa-2,4-dien-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-8-methylundeca-2,4,6-trienoate
  参考文献：
  名称：

  Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide

  摘要：

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.

  DOI：

  10.1021/jo9012833

文献信息

• Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide
  作者：Etienne Fleury、Marie-Isabelle Lannou、Olivia Bistri、François Sautel、Georges Massiot、Ange Pancrazi、Janick Ardisson

  DOI：10.1021/jo9012833

  日期：2009.9.18

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.