3,4-methylene-4'-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)ellagic acid | 1448227-56-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 3,4-methylene-4'-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)ellagic acid
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(12-hydroxy-9,16-dioxo-3,5,10,17-tetraoxapentacyclo[9.6.2.02,6.08,18.015,19]nonadeca-1(18),2(6),7,11(19),12,14-hexaen-13-yl)oxy]oxan-2-yl]methyl acetate
• CAS: 1448227-56-2
• 化学式: C₂₉H₂₄O₁₇
• 分子量: 644.499
• InChiKey: FVWVPMVWBRFVSU-XMCHRIDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  215
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  3,4-methylene-4'-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)ellagic acid 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以85%的产率得到3,4-methylenedioxyellagic acid 4'-O-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Okicamelliaside, a Glucoside of Ellagic Acid with Potent Anti-Degranulation Activity

  摘要：

  Okicamelliaside, a glucoside of ellagic acid with potent anti-degranulation activity, was synthesized from ellagic acid. The regioselectivity, solubility, and high reactivity. of the intermediates throughout the synthesis were obtained by the complementary use of triisopropylsilyl (TIPS) and methoxyethoxymethyl (MEM) protective groups on the aglycone skeleton.

  DOI：

  10.1271/bbb.120966
• 作为产物：
  描述：

  3,3'-bis-O-methoxyethoxymethyl-4-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)ellagic acid 在 potassium carbonate 、 三氟乙酸 、 copper(II) oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 3,4-methylene-4'-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)ellagic acid
  参考文献：
  名称：

  Synthesis of Okicamelliaside, a Glucoside of Ellagic Acid with Potent Anti-Degranulation Activity

  摘要：

  Okicamelliaside, a glucoside of ellagic acid with potent anti-degranulation activity, was synthesized from ellagic acid. The regioselectivity, solubility, and high reactivity. of the intermediates throughout the synthesis were obtained by the complementary use of triisopropylsilyl (TIPS) and methoxyethoxymethyl (MEM) protective groups on the aglycone skeleton.

  DOI：

  10.1271/bbb.120966