(3R,3aS,8bS)-3-((S)-1,2-diacetoxyethyl)-1-oxo-1,3,3a,8b-tetrahydrofuro[3,4-b]benzofuran-3a,6,8,8b-tetrayl tetraacetate | 1350981-43-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: (3R,3aS,8bS)-3-((S)-1,2-diacetoxyethyl)-1-oxo-1,3,3a,8b-tetrahydrofuro[3,4-b]benzofuran-3a,6,8,8b-tetrayl tetraacetate
• 英文别名: [(2S)-2-[(3R,3aS,8bS)-3a,6,8,8b-tetraacetyloxy-1-oxo-3H-furo[3,4-b][1]benzofuran-3-yl]-2-acetyloxyethyl] acetate
• CAS: 1350981-43-9
• 化学式: C₂₄H₂₄O₁₅
• 分子量: 552.446
• InChiKey: YJPSTVQMBBLCNE-IVGWJTKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  193
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  脱氢抗坏血酸 在 吡啶 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 (3R,3aS,8bS)-3-((S)-1,2-diacetoxyethyl)-1-oxo-1,3,3a,8b-tetrahydrofuro[3,4-b]benzofuran-3a,6,8,8b-tetrayl tetraacetate
  参考文献：
  名称：

  A biomimetic synthesis of (−)-ascorbyl phloroglucinol and studies toward the construction of ascorbyl-modified catechin natural products and analogues

  摘要：

  A method for appending the ascorbyl moiety onto the framework of phenolic natural products has been developed. This reaction proceeds in two steps from.-ascorbic acid and employs acetic acid catalysis. Excellent stereoselectivity is observed during C C bond formation between the phenolic compound and dehydroascorbic acid, and the process is also chemoselective for phenol derivatives bearing electron-donating substituents in each of the 1, 3, and 5 positions. Further, good regioselectivity was also observed when phenols lacking an axis of C-2 symmetry were employed. This method has led to the synthesis of (-)-ascorbyl phloroglucinol as well as the tetracyclic core of ascorbyl-modified catechin natural products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.102

文献信息

• A biomimetic synthesis of (−)-ascorbyl phloroglucinol and studies toward the construction of ascorbyl-modified catechin natural products and analogues
  作者：Sneha A. Belapure、Zachary G. Beamer、John E. Bartmess、Shawn R. Campagna

  DOI：10.1016/j.tet.2011.09.102

  日期：2011.12

  A method for appending the ascorbyl moiety onto the framework of phenolic natural products has been developed. This reaction proceeds in two steps from.-ascorbic acid and employs acetic acid catalysis. Excellent stereoselectivity is observed during C C bond formation between the phenolic compound and dehydroascorbic acid, and the process is also chemoselective for phenol derivatives bearing electron-donating substituents in each of the 1, 3, and 5 positions. Further, good regioselectivity was also observed when phenols lacking an axis of C-2 symmetry were employed. This method has led to the synthesis of (-)-ascorbyl phloroglucinol as well as the tetracyclic core of ascorbyl-modified catechin natural products. (C) 2011 Elsevier Ltd. All rights reserved.