batatoside L | 1137099-37-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: batatoside L
• 英文别名: [(2S,3R,4R,5R,6S)-4-hydroxy-6-[(2S,3R,4R,5R,6S)-4-hydroxy-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-6-[[(1R,3S,5S,6R,7R,8R,20S,22R,24R,25S,26S)-7,25,26-trihydroxy-24-(hydroxymethyl)-5-methyl-10-oxo-20-pentyl-2,4,9,21,23-pentaoxatricyclo[20.4.0.03,8]hexacosan-6-yl]oxy]oxan-3-yl]oxy-2-methyl-5-[(E)-3-phenylprop-2-enoyl]oxyoxan-3-yl] dodecanoate
• CAS: 1137099-37-6
• 化学式: C₆₆H₁₀₆O₂₂
• 分子量: 1251.55
• InChiKey: NHNVYAWYZRFGCK-ATKWHSGKSA-N

物化性质

• 沸点：
  1165.3±65.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  88
• 可旋转键数：
  29
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  300
• 氢给体数：
  6
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  batatoside L 在 氢氧化钾 、 水 作用下， 反应 2.0h， 生成 月桂酸 、 (S)-(+)-2-甲基丁酸 、 肉桂酸 、 Operculinic acid E
  参考文献：
  名称：

  Novel acylated lipo-oligosaccharides from the tubers of Ipomoea batatas

  摘要：

  Nine new lipo-oligosaccharides, batatosides H-P, were isolated from the tubers of Ipomoea batatas (Convolvulaceae). Spectral and chemical methods allowed to characterize them as tetra- or penta-saccharides that form a macrolactone with the aglycone, (11S)-hydroxyhexadecanoic acid (jalapinolic acid), the absolute configuration of which was established by Mosher's method. Batatosides L and O showed a weak inhibitory effect on the growth of Hep-2 cells, while the others proved to be inactive. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.022
• 作为产物：
  描述：

  [(2S,3S,4R,5R,6S)-4-[(4-methoxyphenyl)methoxy]-6-[(2S,3S,4R,5R,6S)-4-[(4-methoxyphenyl)methoxy]-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-6-[[(1R,3S,5S,6S,7R,8R,20S,22R,24R,25R,26S)-7,25,26-tris[(4-methoxyphenyl)methoxy]-24-[(4-methoxyphenyl)methoxymethyl]-5-methyl-10-oxo-20-pentyl-2,4,9,21,23-pentaoxatricyclo[20.4.0.03,8]hexacosan-6-yl]oxy]oxan-3-yl]oxy-2-methyl-5-[(E)-3-phenylprop-2-enoyl]oxyoxan-3-yl] dodecanoate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 以81%的产率得到batatoside L
  参考文献：
  名称：

  苦杏仁苷L的全合成

  摘要：

  batatoside L（1）是对喉癌细胞具有细胞毒性的树脂糖苷的总合成，已经以高度趋同的方式完成。在这一总合成过程中，最关键的一步是通过Corey-Nicolaou宏观内酯化方法有效构建18元的宏观内酯框架。

  DOI：

  10.1021/jo101231r

文献信息

• Novel acylated lipo-oligosaccharides from the tubers of Ipomoea batatas
  作者：Yong-Qin Yin、Jun-Song Wang、Jian-Guang Luo、Ling-Yi Kong

  DOI：10.1016/j.carres.2008.12.022

  日期：2009.3

  Nine new lipo-oligosaccharides, batatosides H-P, were isolated from the tubers of Ipomoea batatas (Convolvulaceae). Spectral and chemical methods allowed to characterize them as tetra- or penta-saccharides that form a macrolactone with the aglycone, (11S)-hydroxyhexadecanoic acid (jalapinolic acid), the absolute configuration of which was established by Mosher's method. Batatosides L and O showed a weak inhibitory effect on the growth of Hep-2 cells, while the others proved to be inactive. (C) 2009 Elsevier Ltd. All rights reserved.
• Total Synthesis of Batatoside L
  作者：Lin Xie、San-Yong Zhu、Xiao-Qiu Shen、Li-Li He、Jin-Song Yang

  DOI：10.1021/jo101231r

  日期：2010.8.20

  The total synthesis of batatoside L (1), a resin glycoside possessing cytotoxicity against laryngeal carcinoma cells, has been completed in a highly convergent manner. The most crucial step in this total synthesis was the efficient construction of the 18-membered macrolactone framework through the Corey−Nicolaou macrolactonization approach.

  batatoside L（1）是对喉癌细胞具有细胞毒性的树脂糖苷的总合成，已经以高度趋同的方式完成。在这一总合成过程中，最关键的一步是通过Corey-Nicolaou宏观内酯化方法有效构建18元的宏观内酯框架。