1-O-acetyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,6-di-O-benzyl-7-hydroxyxanthone | 1609192-23-5

• 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-O-acetyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,6-di-O-benzyl-7-hydroxyxanthone
• 英文别名: [(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[1-acetyloxy-7-hydroxy-9-oxo-3,6-bis(phenylmethoxy)xanthen-2-yl]oxan-2-yl]methyl acetate
• CAS: 1609192-23-5
• 化学式: C₄₃H₄₀O₁₆
• 分子量: 812.781
• InChiKey: GXYJLDXKJZDPSL-YVGQFNALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  59
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  206
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,6-di-O-benzyl-7-hydroxyxanthone 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以73%的产率得到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：

  octa-O-acetylmangiferin 在 ammonium acetate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-O-acetyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,6-di-O-benzyl-7-hydroxyxanthone
  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