(Z,1R,2S,3R)-1-(methoxycarbamoyl)-2,3-bis(benzyloxy)-7-triisopropylsilyloxyhept-4-enyl pivalate | 1255955-52-2

• 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: (Z,1R,2S,3R)-1-(methoxycarbamoyl)-2,3-bis(benzyloxy)-7-triisopropylsilyloxyhept-4-enyl pivalate
• 英文别名: [(Z,2R,3S,4R)-1-(methoxyamino)-1-oxo-3,4-bis(phenylmethoxy)-8-tri(propan-2-yl)silyloxyoct-5-en-2-yl] 2,2-dimethylpropanoate
• CAS: 1255955-52-2
• 化学式: C₃₇H₅₇NO₇Si
• 分子量: 655.948
• InChiKey: BMMXDTMTBQTOHC-GVQWGUTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.93
• 重原子数：
  46
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  、 甲氧基胺盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以144.5 mg的产率得到(Z,1R,2S,3R)-1-(methoxycarbamoyl)-2,3-bis(benzyloxy)-7-triisopropylsilyloxyhept-4-enyl 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.