(1S,2S,8aS)-1,2-di(tert-butoxy)-1,2,3,5,6,8a-hexahydroindolizine | 863890-70-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1S,2S,8aS)-1,2-di(tert-butoxy)-1,2,3,5,6,8a-hexahydroindolizine
• 英文别名: (1S,2S,8aS)-1,2-bis[(2-methylpropan-2-yl)oxy]-1,2,3,5,6,8a-hexahydroindolizine
• CAS: 863890-70-4
• 化学式: C₁₆H₂₉NO₂
• 分子量: 267.412
• InChiKey: UZVCLEKDCPHOBC-IHRRRGAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,8aS)-1,2-di(tert-butoxy)-1,2,3,5,6,8a-hexahydroindolizine 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 生成 (+)-lentiginosine
  参考文献：
  名称：

  New Concise Total Synthesis of (+)-Lentiginosine and Some Structural Analogues

  摘要：

  An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.

  DOI：

  10.1021/jo0509408
• 作为产物：
  描述：

  (3S,4S)-3,4-di-tert-butoxy-1-pyrroline N-oxide 在 Grubbs catalyst first generation indium 、 lithium aluminium tetrahydride 、 氯化铵 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 73.75h， 生成 (1S,2S,8aS)-1,2-di(tert-butoxy)-1,2,3,5,6,8a-hexahydroindolizine
  参考文献：
  名称：

  New Concise Total Synthesis of (+)-Lentiginosine and Some Structural Analogues

  摘要：

  An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.

  DOI：

  10.1021/jo0509408

文献信息

• New Concise Total Synthesis of (+)-Lentiginosine and Some Structural Analogues
  作者：Francesca Cardona、Guillermo Moreno、Francesco Guarna、Pierre Vogel、Catherine Schuetz、Pedro Merino、Andrea Goti

  DOI：10.1021/jo0509408

  日期：2005.8.1

  An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.