(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 | 196859-88-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• 英文别名: (1S,5R,6S,7S,11R)-11-(hydroxymethyl)-3,3,7-trimethyl-2,4,8-trioxatricyclo[5.3.1.01,5]undecan-6-ol
• CAS: 196859-88-8
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: ACMCIQRVQZSEBL-TWXYISROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (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 在 吡啶 作用下， 反应 2.0h， 生成 Acetic acid (1S,5R,6S,7S,11R)-6-acetoxy-3,3,7-trimethyl-2,4,8-trioxa-tricyclo[5.3.1.0^1,5]undec-11-ylmethyl ester
  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-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

文献信息

• Chiral Synthons from the Iridoid Glucoside Antirrhinoside − Synthesis of a Carbocyclic Homonucleoside Analogue
  作者：Armandodoriano Bianco、Diana Celona、Sara Di Rita、Marcella Guiso、Cristiana Melchioni、Floriana Umani

  DOI：10.1002/1099-0690(200111)2001:21<4061::aid-ejoc4061>3.0.co;2-3

  日期：2001.11

  have been performed on the bicyclic iridoidic ring, resulting in opening of the dihydropyran ring. A series of chiral synthons having a highly oxygenated cyclopentanoid ring has been prepared, which could be used in the synthesis of nucleoside analogues. We describe herein the synthesis of an acyclovir derivative (DA-146) as an example.

  报道了天然环戊烷单萜葡萄糖苷抗犀草苷的合成改性。对双环环烯丙环进行了一些立体选择性修饰，导致二氢吡喃环打开。已经制备了一系列具有高氧化环戊烷环的手性合成子，可用于合成核苷类似物。我们在此以合成阿昔洛韦衍生物 (DA-146) 为例进行了描述。