(2S,3R,4S,5R)-2-(allyloxy)-4,5-bis(benzyloxy)-tetrahydro-2H-pyran-3-yl pivalate | 1255955-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R)-2-(allyloxy)-4,5-bis(benzyloxy)-tetrahydro-2H-pyran-3-yl pivalate
• 英文别名: [(2S,3R,4S,5R)-4,5-bis(phenylmethoxy)-2-prop-2-enoxyoxan-3-yl] 2,2-dimethylpropanoate
• CAS: 1255955-43-1
• 化学式: C₂₇H₃₄O₆
• 分子量: 454.563
• InChiKey: VQDQGDNABHIKFA-RCTAOEEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R)-2-(allyloxy)-4,5-bis(benzyloxy)-tetrahydro-2H-pyran-3-yl pivalate 在 正丁基锂 、 tris(triphenylphosphine)rhodium(l) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 48.0h， 生成 (2R,3R,4S,5R)-4,5-bis(benzyloxy)-2-(prop-1-en-1-yloxy)tetrahydro-2H-pyran-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：

  (2S,3R,4R,5R)-2-(allyloxy)-tetrahydro-4,5-bis(trimethylsilanyloxy)-2H-pyran-3-yl pivalate 、 苯甲醛 在 三氟甲磺酸三甲基硅酯 、 三乙基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以55%的产率得到(2S,3R,4S,5R)-2-(allyloxy)-4,5-bis(benzyloxy)-tetrahydro-2H-pyran-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.