1,2,4-tri-O-benzoyl-3-O-benzyl-D-glucopyranoside | 1039374-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,4-tri-O-benzoyl-3-O-benzyl-D-glucopyranoside
• CAS: 1039374-58-7
• 化学式: C₃₄H₃₀O₉
• 分子量: 582.607
• InChiKey: RLTKMWAOSPEIBW-OHSUJLOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  43.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  117.59
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,2,4-tri-O-benzoyl-3-O-benzyl-D-glucopyranoside 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 (2S,3S,4S,5R)-3,5,6-Tris-benzoyloxy-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid
  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：

  1,2,4-tri-O-benzoyl-3-O-benzyl-6-O-trityl-D-glucopyranoside 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以73%的产率得到1,2,4-tri-O-benzoyl-3-O-benzyl-D-glucopyranoside
  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