5,6:4',6'-di-O-isopropylidene-antirrhinoside | 196859-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 5,6:4',6'-di-O-isopropylidene-antirrhinoside
• 英文别名: (4aR,6S,7R,8R,8aS)-2,2-dimethyl-6-[[(1S,5R,6S,8R,9R,10S)-3,3,8-trimethyl-2,4,7,11-tetraoxatetracyclo[7.4.0.01,5.06,8]tridec-12-en-10-yl]oxy]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 196859-81-1
• 化学式: C₂₁H₃₀O₁₀
• 分子量: 442.463
• InChiKey: OQWNNNNNEOITBT-PLJXYMTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5,6:4',6'-di-O-isopropylidene-antirrhinoside 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (3aR,5S,5aR,8aR)-7-Benzyl-2,2,5-trimethyl-hexahydro-1,3-dioxa-7-aza-cyclopenta[c]pentalen-5-ol
  参考文献：
  名称：

  Conversion of the Iridoid Glucoside Antirrhinoside into 3-Azabicyclo[3.3.0]octane Building Blocks

  摘要：

  The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12, and 13 in 4 to 5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2-methoxybenzylamine to yield bicyclic pyrrolidines 3, 12, and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N-benzyl and isopropylidene moieties in 12 and 13, respectively.

  DOI：

  10.1021/np9905517
• 作为产物：
  描述：

  叶含龙头花甙 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 丙酮 为溶剂， 以77%的产率得到5,6:4',6'-di-O-isopropylidene-antirrhinoside
  参考文献：
  名称：

  Synthesis of Monoterpene Piperidines from the Iridoid Glucoside Antirrhinoside

  摘要：

  Synthesis of five novel piperidine monoterpene alkaloids (17-21) using the iridoid glucoside antirrhinoside (4) as a synthon is described. Two strategies for their preparation were investigated: the first possible pathway involved an intermediate diol, 13, from which the piperidine ring was expected to be constructed via reaction of its ditosylate with an amine; the second strategy involved a double reductive amination as the key step to the piperidine ring, which proved successful. The stereochemistry of C-5 and C-9 in the obtained piperidine monoterpenes was the same as that reported for alpha-skytanthine (3), a known isolate from Skytanthus acutus (Apocynaceae).

  DOI：

  10.1021/np9702648

文献信息

• Synthesis of Monoterpene Piperidines from the Iridoid Glucoside Antirrhinoside
  作者：Henrik Franzyk、Signe M. Frederiksen、Søren Rosendal Jensen

  DOI：10.1021/np9702648

  日期：1997.10.1

  Synthesis of five novel piperidine monoterpene alkaloids (17-21) using the iridoid glucoside antirrhinoside (4) as a synthon is described. Two strategies for their preparation were investigated: the first possible pathway involved an intermediate diol, 13, from which the piperidine ring was expected to be constructed via reaction of its ditosylate with an amine; the second strategy involved a double reductive amination as the key step to the piperidine ring, which proved successful. The stereochemistry of C-5 and C-9 in the obtained piperidine monoterpenes was the same as that reported for alpha-skytanthine (3), a known isolate from Skytanthus acutus (Apocynaceae).
• Conversion of the Iridoid Glucoside Antirrhinoside into 3-Azabicyclo[3.3.0]octane Building Blocks
  作者：Henrik Franzyk、Signe M. Frederiksen、Søren Rosendal Jensen

  DOI：10.1021/np9905517

  日期：2000.5.1

  The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12, and 13 in 4 to 5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2-methoxybenzylamine to yield bicyclic pyrrolidines 3, 12, and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N-benzyl and isopropylidene moieties in 12 and 13, respectively.