[(3S,8S,13S)-8,13-bis[(2-methylpropan-2-yl)oxycarbonyloxy]-1,6,11-triazatetracyclo[10.3.0.02,6.07,11]pentadecan-3-yl] tert-butyl carbonate | 1400575-88-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: [(3S,8S,13S)-8,13-bis[(2-methylpropan-2-yl)oxycarbonyloxy]-1,6,11-triazatetracyclo[10.3.0.02,6.07,11]pentadecan-3-yl] tert-butyl carbonate
• CAS: 1400575-88-3
• 化学式: C₂₇H₄₅N₃O₉
• 分子量: 555.669
• InChiKey: ULGNCFRMFLYWRU-QDVRNYAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(3S,8S,13S)-8,13-bis[(2-methylpropan-2-yl)oxycarbonyloxy]-1,6,11-triazatetracyclo[10.3.0.02,6.07,11]pentadecan-3-yl] tert-butyl carbonate 、 1-甲氧基-3-三甲基硅氧基-1,3-丁二烯 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 以73%的产率得到[(1S,8aR)-7-oxo-2,3,8,8a-tetrahydro-1H-indolizin-1-yl] tert-butyl carbonate
  参考文献：
  名称：

  A Diastereoselective Cyclic Imine Cycloaddition Strategy To Access Polyhydroxylated Indolizidine Skeleton: Concise Syntheses of (+)-/(−)-Lentiginosines and (−)-2-epi-Steviamine

  摘要：

  We describe in this paper the development of a novel diastereoselective cyclic imine cycloaddition strategy to access the polyhydroxylated indolizidine skeleton and its application in the concise syntheses of (+)-/(-)-lentiginosines and (-)-2-epi-steviamine.

  DOI：

  10.1021/jo3010777
• 作为产物：
  描述：

  (S)-N-chloro-3-[(tert-butoxycarbonyl)oxy]pyrrolidine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以70%的产率得到[(3S,8S,13S)-8,13-bis[(2-methylpropan-2-yl)oxycarbonyloxy]-1,6,11-triazatetracyclo[10.3.0.02,6.07,11]pentadecan-3-yl] tert-butyl carbonate
  参考文献：
  名称：

  A Diastereoselective Cyclic Imine Cycloaddition Strategy To Access Polyhydroxylated Indolizidine Skeleton: Concise Syntheses of (+)-/(−)-Lentiginosines and (−)-2-epi-Steviamine

  摘要：

  We describe in this paper the development of a novel diastereoselective cyclic imine cycloaddition strategy to access the polyhydroxylated indolizidine skeleton and its application in the concise syntheses of (+)-/(-)-lentiginosines and (-)-2-epi-steviamine.

  DOI：

  10.1021/jo3010777

文献信息

• A Diastereoselective Cyclic Imine Cycloaddition Strategy To Access Polyhydroxylated Indolizidine Skeleton: Concise Syntheses of (+)-/(−)-Lentiginosines and (−)-2-<i>epi</i>-Steviamine
  作者：Jia Shao、Jin-Song Yang

  DOI：10.1021/jo3010777

  日期：2012.9.21

  We describe in this paper the development of a novel diastereoselective cyclic imine cycloaddition strategy to access the polyhydroxylated indolizidine skeleton and its application in the concise syntheses of (+)-/(-)-lentiginosines and (-)-2-epi-steviamine.