diethyl [(5R)-N-benzoyl-(2S)-methoxycarbonylpyrrolidin-5-yl]phosphonate | 1338382-31-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl [(5R)-N-benzoyl-(2S)-methoxycarbonylpyrrolidin-5-yl]phosphonate
• 英文别名: methyl (2S,5R)-1-benzoyl-5-diethoxyphosphorylpyrrolidine-2-carboxylate
• CAS: 1338382-31-2
• 化学式: C₁₇H₂₄NO₆P
• 分子量: 369.354
• InChiKey: ITYURDNZCNTKTF-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl [(5R)-N-benzoyl-(2S)-methoxycarbonylpyrrolidin-5-yl]phosphonate 在 2,6-二甲基吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 diethyl [(2R)-N-benzoyl-5-methoxypyrrolidin-2-yl]phosphonate
  参考文献：
  名称：

  Facile synthesis of both enantiomers of (pyrrolidin-2-yl)phosphonate from l-proline

  摘要：

  Diastereoselective introduction of phosphono groups into L-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Benzoyl-L-prolinate preferentially gave trans-phosphorylated products, which could be easily transformed into (S)-(pyrrolidin-2-yl)phosphonates. On the other hand, N-benzyloxycarbonyl-L-prolinate reacted with phosphite to give cis-substituted products, which could be easily transformed into (R)-(pyrrolidin-2-yl)phosphonates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.080
• 作为产物：
  描述：

  1-Benzoyl-2-methoxy-5-(methoxycarbonyl)pyrrolidine 、 亚磷酸三乙酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 diethyl [(5R)-N-benzoyl-(2S)-methoxycarbonylpyrrolidin-5-yl]phosphonate 、 diethyl [N-benzoyl-(2S)-methoxycarbonylpyrrolidin-5-yl]phosphonate
  参考文献：
  名称：

  Facile synthesis of both enantiomers of (pyrrolidin-2-yl)phosphonate from l-proline

  摘要：

  Diastereoselective introduction of phosphono groups into L-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Benzoyl-L-prolinate preferentially gave trans-phosphorylated products, which could be easily transformed into (S)-(pyrrolidin-2-yl)phosphonates. On the other hand, N-benzyloxycarbonyl-L-prolinate reacted with phosphite to give cis-substituted products, which could be easily transformed into (R)-(pyrrolidin-2-yl)phosphonates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.080

文献信息

• Facile synthesis of both enantiomers of (pyrrolidin-2-yl)phosphonate from l-proline
  作者：Shigeo Hirata、Masami Kuriyama、Osamu Onomura

  DOI：10.1016/j.tet.2011.09.080

  日期：2011.12

  Diastereoselective introduction of phosphono groups into L-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Benzoyl-L-prolinate preferentially gave trans-phosphorylated products, which could be easily transformed into (S)-(pyrrolidin-2-yl)phosphonates. On the other hand, N-benzyloxycarbonyl-L-prolinate reacted with phosphite to give cis-substituted products, which could be easily transformed into (R)-(pyrrolidin-2-yl)phosphonates. (C) 2011 Elsevier Ltd. All rights reserved.