(1S,6R,7S,8R,8aR)-1,6,7,8-Tetraacetoxy-5-oxoindolizidine | 151953-17-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (1S,6R,7S,8R,8aR)-1,6,7,8-Tetraacetoxy-5-oxoindolizidine
• CAS: 151953-17-2
• 化学式: C₁₆H₂₁NO₉
• 分子量: 371.344
• InChiKey: MFKKWMIBZBWGLM-VYDRJRHOSA-N

物化性质

• 沸点：
  477.3±45.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.67
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  125.51
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (1S,6R,7S,8R,8aR)-1,6,7,8-Tetraacetoxy-5-oxoindolizidine 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以55%的产率得到Castanospermine tetraacetate
  参考文献：
  名称：

  A concise, enantioselective synthesis of castanospermine

  摘要：

  A stereoselective synthesis of the polyhydroxy indolizidine alkaloids castanospermine (1) and 6,7-diepicastanospermine (4) has been achieved starting from the readily available alcohol 8. Subsequent Sharpless asymmetric epoxidation, followed by the azide displacement of the tosyl group gave the epoxy azide 12. The asymmetric dihydroxylation of 12 with (DHQ)2-PHAL gave the triol 13 in good diastereoselectivity. Alcohol protection, followed by reductive double cyclization of the resulting epoxy azide 17 gave 5-indolizidinone 18, which was then uneventfully converted to 1. On the other hand, the use of (DHQD)2-PHAL in the dihydroxylation of 12 provided a stereoselective preparation of 4.

  DOI：

  10.1021/jo00077a034
• 作为产物：
  描述：

  在 吡啶 作用下， 以 乙醇 为溶剂， 反应 30.0h， 生成 (1S,6R,7S,8R,8aR)-1,6,7,8-Tetraacetoxy-5-oxoindolizidine
  参考文献：
  名称：

  A concise, enantioselective synthesis of castanospermine

  摘要：

  A stereoselective synthesis of the polyhydroxy indolizidine alkaloids castanospermine (1) and 6,7-diepicastanospermine (4) has been achieved starting from the readily available alcohol 8. Subsequent Sharpless asymmetric epoxidation, followed by the azide displacement of the tosyl group gave the epoxy azide 12. The asymmetric dihydroxylation of 12 with (DHQ)2-PHAL gave the triol 13 in good diastereoselectivity. Alcohol protection, followed by reductive double cyclization of the resulting epoxy azide 17 gave 5-indolizidinone 18, which was then uneventfully converted to 1. On the other hand, the use of (DHQD)2-PHAL in the dihydroxylation of 12 provided a stereoselective preparation of 4.

  DOI：

  10.1021/jo00077a034