diethyl (2S,4S)-4-hydroxy-1-[(S)-2-methoxy-2-phenylacetyl]pyrrolidinyl-2-phosphonate | 948832-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl (2S,4S)-4-hydroxy-1-[(S)-2-methoxy-2-phenylacetyl]pyrrolidinyl-2-phosphonate
• CAS: 948832-58-4
• 化学式: C₁₇H₂₆NO₆P
• 分子量: 371.37
• InChiKey: KVWPCNANRHCRGC-JYJNAYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  85.3
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl (2S,4S)-4-hydroxy-1-[(S)-2-methoxy-2-phenylacetyl]pyrrolidinyl-2-phosphonate 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 diethyl (2S,4S)-4-acetoxy-1-[(S)-2-methoxy-2-phenylacetyl]pyrrolidinyl-2-phosphonate
  参考文献：
  名称：

  Enantiomerically pure phosphonate analogues of cis- and trans-4-hydroxyprolines

  摘要：

  All the enantiomers of 0,0-diethyl 4-hydroxypyrrolidinyl-2-phosphonates, phosphonate analogues of cis- and trans-4hydroxyprolines, have been obtained for the first time. The synthetic strategy involved 1,3-dipolar cycloaddition of (R)- and (S)-N-(1-phenylethyl)-C-(diethoxyphosphoryl)nitrones to ally] alcohol and separation of the corresponding 0,0-diethyl 5-(hydroxymethyl)-2-(1-phenylethyl)isoxazolidinyl-3-phosphonates, which were subsequently mesylated and hydrogenated to undergo intramolecular cyclisation. Absolute configurations of the enantiomeric proline phosphonates were established after N- and 0-derivatization with (S)-O-methylmandelic acid employing the Trost model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.006
• 作为产物：
  描述：

  diethyl (2S,4S)-4-[(S)-2-methoxy-2-phenylacetoyloxy]-1-[(S)-2-methoxy-2-phenylacetyl]pyrrolidinyl-2-phosphonate 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 diethyl (2S,4S)-4-hydroxy-1-[(S)-2-methoxy-2-phenylacetyl]pyrrolidinyl-2-phosphonate
  参考文献：
  名称：

  Enantiomerically pure phosphonate analogues of cis- and trans-4-hydroxyprolines

  摘要：

  All the enantiomers of 0,0-diethyl 4-hydroxypyrrolidinyl-2-phosphonates, phosphonate analogues of cis- and trans-4hydroxyprolines, have been obtained for the first time. The synthetic strategy involved 1,3-dipolar cycloaddition of (R)- and (S)-N-(1-phenylethyl)-C-(diethoxyphosphoryl)nitrones to ally] alcohol and separation of the corresponding 0,0-diethyl 5-(hydroxymethyl)-2-(1-phenylethyl)isoxazolidinyl-3-phosphonates, which were subsequently mesylated and hydrogenated to undergo intramolecular cyclisation. Absolute configurations of the enantiomeric proline phosphonates were established after N- and 0-derivatization with (S)-O-methylmandelic acid employing the Trost model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.006