28-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oleanate 3-O-(3,4-O-isopropylidene-2-O-benzoyl-α-L-arabinopyranosyl-(1->3)-2,4-di-O-benzoyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside) | 1039373-79-9

• 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: 28-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oleanate 3-O-(3,4-O-isopropylidene-2-O-benzoyl-α-L-arabinopyranosyl-(1->3)-2,4-di-O-benzoyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside)
• CAS: 1039373-79-9
• 化学式: C₁₀₅H₁₂₂O₂₄Si
• 分子量: 1796.19
• InChiKey: OQFPUNWBMNHQTF-SNXXZORKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.66
• 重原子数：
  130.0
• 可旋转键数：
  24.0
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  284.24
• 氢给体数：
  0.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  28-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oleanate 3-O-(3,4-O-isopropylidene-2-O-benzoyl-α-L-arabinopyranosyl-(1->3)-2,4-di-O-benzoyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside) 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以88%的产率得到28-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oleanate 3-O-(2-O-benzoyl-α-L-arabinopyranosyl-(1->3)-2,4-di-O-benzoyl-β-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
• 作为产物：
  描述：

  phenyl 3,4-O-isopropylidene-2-O-benzoyl-1-thio-α-L-arabinopyranoside 、 28-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oleanate 3-O-(2,4-di-O-benzoyl-β-D-glucopyranoside) 在 N-碘代丁二酰亚胺 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到28-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oleanate 3-O-(3,4-O-isopropylidene-2-O-benzoyl-α-L-arabinopyranosyl-(1->3)-2,4-di-O-benzoyl-6-O-(tert-butyldimethylsilyl)-β-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