(S)-12-hydroxypentadecanoic acid 12-O-β-D-glucopyranosyl-(1->3)-O-[α-L-rhamnopyranosyl-(1->4)]-O-α-L-rhamnopyranosyl-(1->4)-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside | 1400908-78-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (S)-12-hydroxypentadecanoic acid 12-O-β-D-glucopyranosyl-(1->3)-O-[α-L-rhamnopyranosyl-(1->4)]-O-α-L-rhamnopyranosyl-(1->4)-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside
• 英文别名: turpethic acid A；(12S)-12-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6S)-3-hydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentadecanoic acid
• CAS: 1400908-78-2
• 化学式: C₄₅H₈₀O₂₅
• 分子量: 1021.12
• InChiKey: UGQXYJHYUCPHQY-PUPVUCAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  70
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  393
• 氢给体数：
  14
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  (S)-12-hydroxypentadecanoic acid 12-O-β-D-glucopyranosyl-(1->3)-O-[α-L-rhamnopyranosyl-(1->4)]-O-α-L-rhamnopyranosyl-(1->4)-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 硫酸 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 (S)-12-[(R)-α-methoxy-α-phenylacetyloxy]pentadecanoic acid methyl ester
  参考文献：
  名称：

  Resin glycosides from the aerial parts of Operculina turpethum

  摘要：

  Three glycosidic acids, turpethic acids A-C, and two intact resin glycosides, turpethosides A and B, all having a common pentasaccharide moiety and 12-hydroxy fatty acid aglycones of different chain lengths, were obtained from the aerial parts of Operculina turpethum. Their structures were elucidated by spectroscopic analyses and chemical correlations. The aglycones were characterized as 12-hydroxypentadecanoic acid in two compounds, 12-hydroxyhexadecanoic acid in two other components, and 12-hydroxyheptadecanoic acid in the fifth compound, which were all confirmed by synthesis. The absolute configurations of these aglycones were all established as S by Mosher's method. These compounds represent the first examples of resin glycosides with a monohydroxylated 12-hydroxy fatty acid as an aglycone, and one compound is the first described resin glycoside having a hydroxylated C-17 fatty acid as its aglycone. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.05.010
• 作为产物：
  描述：

  (S)-12-hydroxypentadecanoic acid 12-O-(6-O-(S)-2-methylbutyryl)-β-D-glucopyranosyl-(1->3)-O-[4-O-tigloyl-α-L-rhamnopyranosyl-(1->4)]-O-[2-O-(S)-2-methylbutyryl]-α-L-rhamnopyranosyl-(1->4)-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside 在 potassium hydroxide 作用下， 反应 4.0h， 以3 mg的产率得到(S)-12-hydroxypentadecanoic acid 12-O-β-D-glucopyranosyl-(1->3)-O-[α-L-rhamnopyranosyl-(1->4)]-O-α-L-rhamnopyranosyl-(1->4)-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside
  参考文献：
  名称：

  Resin glycosides from the aerial parts of Operculina turpethum

  摘要：

  Three glycosidic acids, turpethic acids A-C, and two intact resin glycosides, turpethosides A and B, all having a common pentasaccharide moiety and 12-hydroxy fatty acid aglycones of different chain lengths, were obtained from the aerial parts of Operculina turpethum. Their structures were elucidated by spectroscopic analyses and chemical correlations. The aglycones were characterized as 12-hydroxypentadecanoic acid in two compounds, 12-hydroxyhexadecanoic acid in two other components, and 12-hydroxyheptadecanoic acid in the fifth compound, which were all confirmed by synthesis. The absolute configurations of these aglycones were all established as S by Mosher's method. These compounds represent the first examples of resin glycosides with a monohydroxylated 12-hydroxy fatty acid as an aglycone, and one compound is the first described resin glycoside having a hydroxylated C-17 fatty acid as its aglycone. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.05.010