benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside | 1039374-26-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside
• 英文别名: benzyl (2S,3S,4S,5R,6R)-3,5,6-tribenzoyloxy-4-hydroxyoxane-2-carboxylate
• CAS: 1039374-26-9
• 化学式: C₃₄H₂₈O₁₀
• 分子量: 596.59
• InChiKey: BSOCOKRUEXOJEV-RVSVHKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-O-isopropylidene-2-O-(2-azidomethylbenzoyl)-1-thio-α-L-arabinopyranoside 、 benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以81%的产率得到3,4-O-isopropylidene-2-O-(2-azidomethylbenzoyl)-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
• 作为产物：
  描述：

  、 溴甲苯 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以175 mg的产率得到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

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.