5,6-O-isopropylidene antirrhinoside | 196859-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-O-isopropylidene antirrhinoside
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-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]oxane-3,4,5-triol
• CAS: 196859-83-3
• 化学式: C₁₈H₂₆O₁₀
• 分子量: 402.398
• InChiKey: CAVZGDHHEBYRPJ-PRCDFJNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5,6-O-isopropylidene antirrhinoside 在 platinum on activated charcoal sodium tetrahydroborate 、 氢气 、 β-glucosidase 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 15.0~25.0 ℃ 、101.33 kPa 条件下， 反应 74.5h， 生成 (1S,5R,6S,7S,11R)-11-Hydroxymethyl-3,3,7-trimethyl-2,4,8-trioxa-tricyclo[5.3.1.0^1,5]undecan-6-ol
  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
• 作为产物：
  描述：

  5,6:4',6'-di-O-isopropylidene-antirrhinoside 在 溶剂黄146 作用下， 反应 5.0h， 以93%的产率得到5,6-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).