methyl (5Z,8R,9E,14Z)-8-[[(2R,3R,4S,5R,6R)-6-[(2R)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]icosa-5,9,14-trienoate | 1448441-46-0

• 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: methyl (5Z,8R,9E,14Z)-8-[[(2R,3R,4S,5R,6R)-6-[(2R)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]icosa-5,9,14-trienoate
• CAS: 1448441-46-0
• 化学式: C₃₀H₅₂O₁₀
• 分子量: 572.737
• InChiKey: PNVCLQKQJOCNOM-IZLYOCIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  40
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 rosenmund catalyst 、 四丁基氟化铵 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (5Z,8R,9E,14Z)-8-[[(2R,3R,4S,5R,6R)-6-[(2R)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]icosa-5,9,14-trienoate
  参考文献：
  名称：

  A stereoselective method for the construction of the C8′–O–C6″ ether of nigricanoside-A: synthesis of simple models for the C20 lipid chain/galactosyl glycerol segment

  摘要：

  A method for the stereoselective construction of the C8'-O-C6" ether of nigricanoside-A, an antimitotic natural product from the green alga Avrainvillea nigricans, has been developed based on chirality-transferring Ireland-Claisen rearrangement. The method was successfully applied to the synthesis of simple models for the C20 lipid chain/galactosyl glycerol segment of the natural product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.085

文献信息

• A stereoselective method for the construction of the C8′–O–C6″ ether of nigricanoside-A: synthesis of simple models for the C20 lipid chain/galactosyl glycerol segment
  作者：Naoto Kinashi、Kenshu Fujiwara、Takayuki Tsunoda、Ryo Katoono、Hidetoshi Kawai、Takanori Suzuki

  DOI：10.1016/j.tetlet.2013.06.085

  日期：2013.8

  A method for the stereoselective construction of the C8'-O-C6" ether of nigricanoside-A, an antimitotic natural product from the green alga Avrainvillea nigricans, has been developed based on chirality-transferring Ireland-Claisen rearrangement. The method was successfully applied to the synthesis of simple models for the C20 lipid chain/galactosyl glycerol segment of the natural product. (C) 2013 Elsevier Ltd. All rights reserved.