(6bS,9R,9aR)-9-((S)-1,2-dihydroxyethyl)-6,6b,9a-trihydroxy-2,3,9,9a-tetrahydro-1H-furo[3',4':4,5]furo[2,3-f]chromen-7(6bH)-one | 1350802-54-8

• 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: (6bS,9R,9aR)-9-((S)-1,2-dihydroxyethyl)-6,6b,9a-trihydroxy-2,3,9,9a-tetrahydro-1H-furo[3',4':4,5]furo[2,3-f]chromen-7(6bH)-one
• 英文别名: (11S,14R,15R)-14-[(1S)-1,2-dihydroxyethyl]-9,11,15-trihydroxy-6,13,16-trioxatetracyclo[8.6.0.02,7.011,15]hexadeca-1(10),2(7),8-trien-12-one
• CAS: 1350802-54-8
• 化学式: C₁₅H₁₆O₉
• 分子量: 340.287
• InChiKey: PFZIXGZDSGSQJM-AZEZGGBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  间苯三酚 在 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 10.0h， 生成 (6bS,9R,9aR)-9-((S)-1,2-dihydroxyethyl)-6,6b,9a-trihydroxy-2,3,9,9a-tetrahydro-1H-furo[3',4':4,5]furo[2,3-f]chromen-7(6bH)-one 、 (7aR,8R,10aS)-8-((S)-1,2-dihydroxyethyl)-5,7a,10a-trihydroxy-3,4,7a,8-tetrahydro-2H-furo[3',4':4,5]furo[2,3-h]chromen-10(10aH)-one
  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.