[(3R,4S,5R,6R)-1-methoxy-2-oxo-4,5-bis(phenylmethoxy)-6-[(1S)-1-(2,2,2-trifluoroacetyl)oxy-3-tri(propan-2-yl)silyloxypropyl]piperidin-3-yl] 2,2-dimethylpropanoate | 1255955-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3R,4S,5R,6R)-1-methoxy-2-oxo-4,5-bis(phenylmethoxy)-6-[(1S)-1-(2,2,2-trifluoroacetyl)oxy-3-tri(propan-2-yl)silyloxypropyl]piperidin-3-yl] 2,2-dimethylpropanoate
• CAS: 1255955-53-3
• 化学式: C₃₉H₅₆F₃NO₉Si
• 分子量: 767.956
• InChiKey: BNGQSNMQWNTXRX-OWCNLOMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.94
• 重原子数：
  53
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(3R,4S,5R,6R)-1-methoxy-2-oxo-4,5-bis(phenylmethoxy)-6-[(1S)-1-(2,2,2-trifluoroacetyl)oxy-3-tri(propan-2-yl)silyloxypropyl]piperidin-3-yl] 2,2-dimethylpropanoate 在 氨 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.5h， 以81.7 mg的产率得到(3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-(3'-triisopropylsilanyloxy-(S)-1'-hydroxypropyl)-1-methoxy-2-oxopiperidin-3-yl pivalate
  参考文献：
  名称：

  Diastereoselective Nitrenium Ion-Mediated Cyclofunctionalization: Total Synthesis of (+)-Castanospermine

  摘要：

  The asymmetric total synthesis of the cc-glucosidase inhibitor (+)-castanospermine is reported. The central theme in our approach to this polyhydroxylated alkaloid is the simultaneous generation of the piperidine ring and the C-1/8a erythro stereodiad through the diastereoselective, oxamidation of an unsaturated O-alkyl hydroxamate. This process is believed to proceed sequentially via singlet acylnitrenium and aziridinium ion intermediates.

  DOI：

  10.1021/ol102371x
• 作为产物：
  描述：

  (Z,1R,2S,3R)-1-(methoxycarbamoyl)-2,3-bis(benzyloxy)-7-triisopropylsilyloxyhept-4-enyl pivalate 、 三氟乙酸 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 [(3R,4S,5R,6R)-1-methoxy-2-oxo-4,5-bis(phenylmethoxy)-6-[(1S)-1-(2,2,2-trifluoroacetyl)oxy-3-tri(propan-2-yl)silyloxypropyl]piperidin-3-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Diastereoselective Nitrenium Ion-Mediated Cyclofunctionalization: Total Synthesis of (+)-Castanospermine

  摘要：

  The asymmetric total synthesis of the cc-glucosidase inhibitor (+)-castanospermine is reported. The central theme in our approach to this polyhydroxylated alkaloid is the simultaneous generation of the piperidine ring and the C-1/8a erythro stereodiad through the diastereoselective, oxamidation of an unsaturated O-alkyl hydroxamate. This process is believed to proceed sequentially via singlet acylnitrenium and aziridinium ion intermediates.

  DOI：

  10.1021/ol102371x

文献信息

• Diastereoselective Nitrenium Ion-Mediated Cyclofunctionalization: Total Synthesis of (+)-Castanospermine
  作者：Edward G. Bowen、Duncan J. Wardrop

  DOI：10.1021/ol102371x

  日期：2010.11.19

  The asymmetric total synthesis of the cc-glucosidase inhibitor (+)-castanospermine is reported. The central theme in our approach to this polyhydroxylated alkaloid is the simultaneous generation of the piperidine ring and the C-1/8a erythro stereodiad through the diastereoselective, oxamidation of an unsaturated O-alkyl hydroxamate. This process is believed to proceed sequentially via singlet acylnitrenium and aziridinium ion intermediates.