dimethyl (1R,2S)-1,2-dihydroxy-3-(4-methoxycarbonyl-1,2,3-triazol-1-yl)propylphosphonate | 716162-57-1

• 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: dimethyl (1R,2S)-1,2-dihydroxy-3-(4-methoxycarbonyl-1,2,3-triazol-1-yl)propylphosphonate
• 英文别名: methyl 1-[(2S,3R)-3-dimethoxyphosphoryl-2,3-dihydroxypropyl]triazole-4-carboxylate
• CAS: 716162-57-1
• 化学式: C₉H₁₆N₃O₇P
• 分子量: 309.216
• InChiKey: XEFPVYBDCNSALR-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dimethyl (1R,2S)-1,2-dihydroxy-3-(4-methoxycarbonyl-1,2,3-triazol-1-yl)propylphosphonate 在 Dowex 50W*4(H⁺) 、 氨 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 189.5h， 生成 O-methyl (1R,2S)-3-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-dihydroxypropylphosphonic acid
  参考文献：
  名称：

  Synthesis of (1R,2S)- and (1S,2S)-3-(4-carbamoyl-1,2,3-triazol-1-yl)-1,2-dihydroxypropylphosphonates

  摘要：

  Good regioselectivity (86:14 and 80:20) was observed in the 1,3-dipolar cycloaddition of methyl propiolate to diastereoisomeric dimethyl (1R,2S)- and (1S,2S)-3-azido-2-benzyloxy-1-hydroxypropylphosphonates. The major 4-Inethoxycarbonyl regioisomers were transformed into O-methyl (1R,2S)- and (1S,2S)-3-(4-carbamoyl-1,2,3-triazol-1-yl)-1,2-dihydroxypropylphosphonic acids, structural analogues of ribavirin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.03.025
• 作为产物：
  描述：

  dimethyl (1R,2S)-3-azido-2-benzyloxy-1-hydroxypropylphosphonate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 172.0h， 生成 dimethyl (1R,2S)-1,2-dihydroxy-3-(4-methoxycarbonyl-1,2,3-triazol-1-yl)propylphosphonate
  参考文献：
  名称：

  Synthesis of (1R,2S)- and (1S,2S)-3-(4-carbamoyl-1,2,3-triazol-1-yl)-1,2-dihydroxypropylphosphonates

  摘要：

  Good regioselectivity (86:14 and 80:20) was observed in the 1,3-dipolar cycloaddition of methyl propiolate to diastereoisomeric dimethyl (1R,2S)- and (1S,2S)-3-azido-2-benzyloxy-1-hydroxypropylphosphonates. The major 4-Inethoxycarbonyl regioisomers were transformed into O-methyl (1R,2S)- and (1S,2S)-3-(4-carbamoyl-1,2,3-triazol-1-yl)-1,2-dihydroxypropylphosphonic acids, structural analogues of ribavirin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.03.025

文献信息

• Synthesis of (1R,2S)- and (1S,2S)-3-(4-carbamoyl-1,2,3-triazol-1-yl)-1,2-dihydroxypropylphosphonates
  作者：Andrzej E. Wróblewski、Iwona E. Głowacka

  DOI：10.1016/j.tetasy.2004.03.025

  日期：2004.5

  Good regioselectivity (86:14 and 80:20) was observed in the 1,3-dipolar cycloaddition of methyl propiolate to diastereoisomeric dimethyl (1R,2S)- and (1S,2S)-3-azido-2-benzyloxy-1-hydroxypropylphosphonates. The major 4-Inethoxycarbonyl regioisomers were transformed into O-methyl (1R,2S)- and (1S,2S)-3-(4-carbamoyl-1,2,3-triazol-1-yl)-1,2-dihydroxypropylphosphonic acids, structural analogues of ribavirin. (C) 2004 Elsevier Ltd. All rights reserved.