1,7-Di-O-acetyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,6-di-O-benzylxanthone | 31002-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1,7-Di-O-acetyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,6-di-O-benzylxanthone
• 英文别名: 3,6-Di-O-benzyl-1,2',3',4',6',7-hexa-O-acetylmangiferin
• CAS: 31002-09-2
• 化学式: C₄₅H₄₂O₁₇
• 分子量: 854.818
• InChiKey: YBPPWAMUOFRGMV-DHWGNVQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  62.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  215.7
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  1,7-Di-O-acetyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,6-di-O-benzylxanthone 在 ammonium acetate 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 甲醇 、 氯仿 、 水 、 丙酮 为溶剂， 反应 5.0h， 生成 1-O-acetyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,6-di-O-benzyl-7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)xanthone
  参考文献：
  名称：

  Semi-synthesis of neomangiferin from mangiferin

  摘要：

  Neomangiferin, a natural xanthone derivative bearing both O- and C-glucosides, was isolated from the leaves of Gentiana asclepiadea L and has shown potential anti-diabetic activity. We describe herein the first semi-synthesis of neomangiferin from the natural C-glucoside mangiferin and glucose. The developed synthesis presents a facile protection strategy using Jurd's method to distinguish the different phenolic hydroxyl groups. Following this strategy, the regioselective protection of 1,3,6-hydroxyl groups was accomplished and neomangiferin was prepared by glycosylation under the phase-transfer catalysis conditions. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.129
• 作为产物：
  描述：

  Mangiferin 在 sodium acetate 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 1,7-Di-O-acetyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,6-di-O-benzylxanthone
  参考文献：
  名称：

  Semi-synthesis of neomangiferin from mangiferin

  摘要：

  Neomangiferin, a natural xanthone derivative bearing both O- and C-glucosides, was isolated from the leaves of Gentiana asclepiadea L and has shown potential anti-diabetic activity. We describe herein the first semi-synthesis of neomangiferin from the natural C-glucoside mangiferin and glucose. The developed synthesis presents a facile protection strategy using Jurd's method to distinguish the different phenolic hydroxyl groups. Following this strategy, the regioselective protection of 1,3,6-hydroxyl groups was accomplished and neomangiferin was prepared by glycosylation under the phase-transfer catalysis conditions. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.129