(3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(3'-triisopropylsilanyloxy-(S)-1'-hydroxypropyl)-piperidin-3-yl pivalate | 1255955-56-6

• 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: (3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(3'-triisopropylsilanyloxy-(S)-1'-hydroxypropyl)-piperidin-3-yl pivalate
• 英文别名: [(3S,4R,5R,6R)-6-[(1S)-1-hydroxy-3-tri(propan-2-yl)silyloxypropyl]-4,5-bis(phenylmethoxy)piperidin-3-yl] 2,2-dimethylpropanoate
• CAS: 1255955-56-6
• 化学式: C₃₆H₅₇NO₆Si
• 分子量: 627.937
• InChiKey: YYPRXTUCIBPJQN-VHFAWWBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.03
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(3'-triisopropylsilanyloxy-(S)-1'-hydroxypropyl)-piperidin-3-yl pivalate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到(3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(3'-hydroxy-(S)-1'-hydroxypropyl)-piperidin-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：

  (3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-(3'-triisopropylsilanyloxy-(S)-1'-hydroxypropyl)-2-oxopiperidin-3-yl pivalate 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到(3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(3'-triisopropylsilanyloxy-(S)-1'-hydroxypropyl)-piperidin-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

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.