diisopropyl (1R,2R,3S)-1,2,3-trihydroxy-2,3-O-isopropylidene-4-[(4-methoxycarbonyl)-1,2,3-triazol-1-yl]butylphosphonate | 875113-00-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diisopropyl (1R,2R,3S)-1,2,3-trihydroxy-2,3-O-isopropylidene-4-[(4-methoxycarbonyl)-1,2,3-triazol-1-yl]butylphosphonate
• 英文别名: methyl 1-[[(4S,5R)-5-[(R)-hydroxy-[oxido-di(propan-2-yloxy)phosphaniumyl]methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]triazole-4-carboxylate
• CAS: 875113-00-1
• 化学式: C₁₇H₃₀N₃O₈P
• 分子量: 435.414
• InChiKey: RGRWOBWDPOQBPH-SQWLQELKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  diisopropyl (1R,2R,3S)-1,2,3-trihydroxy-2,3-O-isopropylidene-4-[(4-methoxycarbonyl)-1,2,3-triazol-1-yl]butylphosphonate 在 氨 、 silver(l) oxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 216.0h， 生成 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 、 丙炔酸甲酯 在 copper(l) chloride 作用下， 以 水 为溶剂， 反应 96.0h， 以99%的产率得到diisopropyl (1R,2R,3S)-1,2,3-trihydroxy-2,3-O-isopropylidene-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

文献信息

• Synthesis of four enantiomerically pure 4-(4-carbamoyl-1,2,3-triazol-1-yl)-2,3-dihydroxy-1-methoxybutylphosphonic acids
  作者：Andrzej E. Wróblewski、Iwona E. Głowacka

  DOI：10.1016/j.tetasy.2005.11.010

  日期：2005.12

  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.