(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(6-piperazin-1-yl-pyridin-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester | 915207-13-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(6-piperazin-1-yl-pyridin-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 915207-13-5
• 化学式: C₂₂H₂₉N₃O₁₀
• 分子量: 495.486
• InChiKey: PAJBLEDGRSZNHH-YIUJWAEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.44
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  151.82
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(6-piperazin-1-yl-pyridin-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 N-甲基吡咯烷酮 、 lithium hydroxide 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 22.0h， 生成
  参考文献：
  名称：

  Gram Scale Synthesis of the Glucuronide Metabolite of ABT-724

  摘要：

  A gram scale synthesis of the glucuronide metabolite of ABT-724 is reported. Glycosidic coupling between a trichloroacetimidate glucuronyl donor and a Cbz-protected hydroxypyridylpiperazine glycosyl acceptor is the key step in the synthesis, since attempts to directly glucuronidate the aglycon, aglycon derivatives, and other truncated glycosyl acceptors were unsuccessful. The route was used to produce 2.1 g of metabolite in eight steps from 2-chloro-5-hydroxypyridine in 21% overall yield.

  DOI：

  10.1021/jo0611972
• 作为产物：
  描述：

  4-[5-((2S,3R,4S,5S,6S)-3,4,5-Triacetoxy-6-methoxycarbonyl-tetrahydro-pyran-2-yloxy)-pyridin-2-yl]-piperazine-1-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 8.0h， 生成 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(6-piperazin-1-yl-pyridin-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Gram Scale Synthesis of the Glucuronide Metabolite of ABT-724

  摘要：

  A gram scale synthesis of the glucuronide metabolite of ABT-724 is reported. Glycosidic coupling between a trichloroacetimidate glucuronyl donor and a Cbz-protected hydroxypyridylpiperazine glycosyl acceptor is the key step in the synthesis, since attempts to directly glucuronidate the aglycon, aglycon derivatives, and other truncated glycosyl acceptors were unsuccessful. The route was used to produce 2.1 g of metabolite in eight steps from 2-chloro-5-hydroxypyridine in 21% overall yield.

  DOI：

  10.1021/jo0611972