[(2R)-1-[dimethoxy(oxido)phosphaniumyl]-4-[6-[[(4-methoxyphenyl)-diphenylmethyl]amino]purin-9-yl]butan-2-yl] (2S)-2-methoxy-2-phenylacetate | 1345025-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [(2R)-1-[dimethoxy(oxido)phosphaniumyl]-4-[6-[[(4-methoxyphenyl)-diphenylmethyl]amino]purin-9-yl]butan-2-yl] (2S)-2-methoxy-2-phenylacetate
• CAS: 1345025-28-6
• 化学式: C₄₀H₄₂N₅O₇P
• 分子量: 735.777
• InChiKey: UQQIXHHJLCCDQW-VHFKIGOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  53
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R)-1-[dimethoxy(oxido)phosphaniumyl]-4-[6-[[(4-methoxyphenyl)-diphenylmethyl]amino]purin-9-yl]butan-2-yl] (2S)-2-methoxy-2-phenylacetate 在 lithium hydroxide monohydrate 作用下， 以 甲醇 、 水 为溶剂， 以74%的产率得到dimethyl (R)-(2-hydroxy-4-(6-(((4-methoxyphenyl)diphenylmethyl)amino)-9H-purin-9-yl)butyl)phosphonate
  参考文献：
  名称：

  Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)

  摘要：

  A synthetic pathway to new acyclonucleoside phosphonates, as analogues of Adefovir, is described. The reduction of an acyclonucleoside beta-ketophosphonate, readily available from the nucleobase and benzyl-acrylate, afforded a mixture of (R)- and (S)-beta-hydroxyphosphonate derivatives which was resolved. The assignment of the absolute configuration was proposed on the basis of NMR studies and was supported by molecular modelling studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.010
• 作为产物：
  描述：

  N-9-(2-benzyloxycarbonylethyl)adenine 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 [(2R)-1-[dimethoxy(oxido)phosphaniumyl]-4-[6-[[(4-methoxyphenyl)-diphenylmethyl]amino]purin-9-yl]butan-2-yl] (2S)-2-methoxy-2-phenylacetate
  参考文献：
  名称：

  Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)

  摘要：

  A synthetic pathway to new acyclonucleoside phosphonates, as analogues of Adefovir, is described. The reduction of an acyclonucleoside beta-ketophosphonate, readily available from the nucleobase and benzyl-acrylate, afforded a mixture of (R)- and (S)-beta-hydroxyphosphonate derivatives which was resolved. The assignment of the absolute configuration was proposed on the basis of NMR studies and was supported by molecular modelling studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.010

文献信息

• Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)
  作者：Mahesh Kasthuri、Laurent Chaloin、Christian Périgaud、Suzanne Peyrottes

  DOI：10.1016/j.tetasy.2011.08.010

  日期：2011.7

  A synthetic pathway to new acyclonucleoside phosphonates, as analogues of Adefovir, is described. The reduction of an acyclonucleoside beta-ketophosphonate, readily available from the nucleobase and benzyl-acrylate, afforded a mixture of (R)- and (S)-beta-hydroxyphosphonate derivatives which was resolved. The assignment of the absolute configuration was proposed on the basis of NMR studies and was supported by molecular modelling studies. (C) 2011 Elsevier Ltd. All rights reserved.