diisopropyl (1R,2R,3S)-2,3-dihydroxy-2,3-O-isopropylidene-1-methoxy-4-[(4-methoxycarbonyl)-1,2,3-triazol-1-yl]butylphosphonate | 875113-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diisopropyl (1R,2R,3S)-2,3-dihydroxy-2,3-O-isopropylidene-1-methoxy-4-[(4-methoxycarbonyl)-1,2,3-triazol-1-yl]butylphosphonate
• CAS: 875113-06-7
• 化学式: C₁₈H₃₂N₃O₈P
• 分子量: 449.441
• InChiKey: ZKOMDNFFDTUYHJ-ZMSDIMECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  120.23
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  diisopropyl (1R,2R,3S)-2,3-dihydroxy-2,3-O-isopropylidene-1-methoxy-4-[(4-methoxycarbonyl)-1,2,3-triazol-1-yl]butylphosphonate 在 氨 作用下， 以 甲醇 为溶剂， 反应 120.0h， 以51%的产率得到diisopropyl (1R,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
• 作为产物：
  描述：

  diisopropyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate 在 copper(l) chloride 、 silver(l) oxide 作用下， 以 氯仿 、 水 为溶剂， 反应 192.0h， 生成 diisopropyl (1R,2R,3S)-2,3-dihydroxy-2,3-O-isopropylidene-1-methoxy-4-[(4-methoxycarbonyl)-1,2,3-triazol-1-yl]butylphosphonate
  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