diisopropyl (1S,2R,3S)-4-(4-carbamoyl-1,2,3-triazol-1-yl)-2,3-dihydroxy-2,3-O-isopropylidene-1-methoxybutylphosphonate | 875113-11-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diisopropyl (1S,2R,3S)-4-(4-carbamoyl-1,2,3-triazol-1-yl)-2,3-dihydroxy-2,3-O-isopropylidene-1-methoxybutylphosphonate
• CAS: 875113-11-4
• 化学式: C₁₇H₃₁N₄O₇P
• 分子量: 434.429
• InChiKey: LTQLFIKAVQLYSO-LZWOXQAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  137.02
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  diisopropyl (1S,2R,3S)-4-(4-carbamoyl-1,2,3-triazol-1-yl)-2,3-dihydroxy-2,3-O-isopropylidene-1-methoxybutylphosphonate 在 Dowex 50W 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.5h， 以52%的产率得到diisopropyl (1S,2R,3S)-4-(4-carbamoyl-1,2,3-triazol-1-yl)-2,3-dihydroxy-1-methoxybutylphosphonate
  参考文献：
  名称：

  Synthesis of four enantiomerically pure 4-(4-carbamoyl-1,2,3-triazol-1-yl)-2,3-dihydroxy-1-methoxybutylphosphonic acids

  摘要：

  CuCl-catalysed cycloaddition of methyl propiolate to O,O-diisopropyl (1S,2R,3S)- and (1R,2R,3S)-, or O,O-dibenzyl (1S,2R,3S)-, (1R,2R,3S)-, (1S,2R,3R)- and (1R,2R,3R)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonates followed by methylation of HO-C-1, ammonolysis of methoxycarbonyl groups and hydrolysis of isopropylidene acetals led to diisopropyl (1S,2,R,3S)- and (1R,2R,3S)-4-(4-carbamoyl-1,2,3-triazol-1-yl)-2,3-dihydroxy-1-methoxybutylphosphonates or, after hydrogenolytic removal of benzyl groups, to (1S,2R,3S)-, (1R,2R,3S)-, (1S,2R,3R)- and (1R,2R,3R)-4-(4-carbamoyl-1,2,3-triazol-1-yl)-2,3-dihydroxy-1-methoxybutylphosphonic acids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.010
• 作为产物：
  描述：

  diisopropyl (1S,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate 在 氨 、 silver(l) oxide 作用下， 以 甲醇 、 氯仿 、 甲苯 为溶剂， 反应 220.0h， 生成 diisopropyl (1S,2R,3S)-4-(4-carbamoyl-1,2,3-triazol-1-yl)-2,3-dihydroxy-2,3-O-isopropylidene-1-methoxybutylphosphonate
  参考文献：
  名称：

  Synthesis of four enantiomerically pure 4-(4-carbamoyl-1,2,3-triazol-1-yl)-2,3-dihydroxy-1-methoxybutylphosphonic acids

  摘要：

  CuCl-catalysed cycloaddition of methyl propiolate to O,O-diisopropyl (1S,2R,3S)- and (1R,2R,3S)-, or O,O-dibenzyl (1S,2R,3S)-, (1R,2R,3S)-, (1S,2R,3R)- and (1R,2R,3R)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonates followed by methylation of HO-C-1, ammonolysis of methoxycarbonyl groups and hydrolysis of isopropylidene acetals led to diisopropyl (1S,2,R,3S)- and (1R,2R,3S)-4-(4-carbamoyl-1,2,3-triazol-1-yl)-2,3-dihydroxy-1-methoxybutylphosphonates or, after hydrogenolytic removal of benzyl groups, to (1S,2R,3S)-, (1R,2R,3S)-, (1S,2R,3R)- and (1R,2R,3R)-4-(4-carbamoyl-1,2,3-triazol-1-yl)-2,3-dihydroxy-1-methoxybutylphosphonic acids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.010