2''-epi-betavulgaroside III | 168111-48-6

• 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: 2''-epi-betavulgaroside III
• 英文别名: beta-D-Glucopyranosiduronic acid, (3beta)-28-(beta-D-glucopyranosyloxy)-28-oxoolean-12-en-3-yl 3-O-[(1S,2S)-2-carboxy-1-(carboxymethoxy)-2-hydroxyethyl]-；(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(1S,2S)-2-carboxy-1-(carboxymethoxy)-2-hydroxyethoxy]-3,5-dihydroxyoxane-2-carboxylic acid
• CAS: 168111-48-6
• 化学式: C₄₇H₇₂O₂₀
• 分子量: 957.077
• InChiKey: GNCYMXULNXKROG-SSBHQBQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  67
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  326
• 氢给体数：
  10
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  在 sodium methylate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以15 mg的产率得到2''-epi-betavulgaroside III
  参考文献：
  名称：

  Synthesis of Betavulgaroside III, a Representative Triterpene seco-Glycoside

  摘要：

  Triterpene seco-glycosides constitute a small family of the plant saponins which feature a terminal seco-saccharide appendage deriving supposedly from oxidative scission of a monosaccharide unit. Herein, we have developed synthetic approaches for the first time to the access to these molecules. Betavulgaroside III (1), a representative congener occurring in Beta vulgaris and Achyranthes fauriei, is successfully synthesized in a total of 31 steps with L-arabinose, D-glucose, and oleanolic acid as starting materials. The longest linear sequence requires 23 steps and in an overall 0.9% yield (from D-glucose). The synthesis features oxidative elaboration of the seco-saccharide unit prior to assembly of the triterpene 3,28-bisglycoside. This tactic has been proven superior, in the attempts to the synthesis of the more easily accessible 2 ''-epi-betavulgaroside III (2), to that employing oxidative cleavage of the terminal saccharide unit at an advanced triterpene 3,28-bisglycoside scaffold.

  DOI：

  10.1021/jo800669h

文献信息

• Synthesis of Betavulgaroside III, a Representative Triterpene <i>seco</i>-Glycoside
  作者：Shilei Zhu、Yingxia Li、Biao Yu

  DOI：10.1021/jo800669h

  日期：2008.7.1

  Triterpene seco-glycosides constitute a small family of the plant saponins which feature a terminal seco-saccharide appendage deriving supposedly from oxidative scission of a monosaccharide unit. Herein, we have developed synthetic approaches for the first time to the access to these molecules. Betavulgaroside III (1), a representative congener occurring in Beta vulgaris and Achyranthes fauriei, is successfully synthesized in a total of 31 steps with L-arabinose, D-glucose, and oleanolic acid as starting materials. The longest linear sequence requires 23 steps and in an overall 0.9% yield (from D-glucose). The synthesis features oxidative elaboration of the seco-saccharide unit prior to assembly of the triterpene 3,28-bisglycoside. This tactic has been proven superior, in the attempts to the synthesis of the more easily accessible 2 ''-epi-betavulgaroside III (2), to that employing oxidative cleavage of the terminal saccharide unit at an advanced triterpene 3,28-bisglycoside scaffold.