3,4-O-isopropylidene-α-L-arabinopyranosyl-(1->3)-[benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside] | 1039374-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-O-isopropylidene-α-L-arabinopyranosyl-(1->3)-[benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside]
• CAS: 1039374-32-7
• 化学式: C₄₂H₄₀O₁₄
• 分子量: 768.771
• InChiKey: VPENHYCTLKARDI-AZVQZDHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  56.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  171.58
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  3,4-O-isopropylidene-α-L-arabinopyranosyl-(1->3)-[benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside] 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  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
• 作为产物：
  描述：

  3,4-O-isopropylidene-2-O-(2-azidomethylbenzoyl)-α-L-arabinopyranosyl-(1->3)-[benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside] 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到3,4-O-isopropylidene-α-L-arabinopyranosyl-(1->3)-[benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside]
  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