diethyl (S)-hydroxy {(S)-1-[(R)-1-phenylethyl]aziridin-2-yl}methylphosphonate | 945676-57-3

• 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: diethyl (S)-hydroxy {(S)-1-[(R)-1-phenylethyl]aziridin-2-yl}methylphosphonate
• 英文别名: (S)-[diethoxy(oxido)phosphaniumyl]-[(2S)-1-[(1R)-1-phenylethyl]aziridin-2-yl]methanol
• CAS: 945676-57-3
• 化学式: C₁₅H₂₄NO₄P
• 分子量: 313.334
• InChiKey: CVYCJPOAEHCHPZ-BAWNGUDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (S)-hydroxy {(S)-1-[(R)-1-phenylethyl]aziridin-2-yl}methylphosphonate 在 叠氮基三甲基硅烷 作用下， 反应 96.0h， 以85%的产率得到diethyl (1S,2S)-3-azido-2-[(R)-1-phenylethyl]amino-1-hydroxypropylphosphonate
  参考文献：
  名称：

  Synthesis of four enantiomers of 2,3-di(N-Boc-amino)-1-hydroxypropylphosphonates

  摘要：

  Enantiomerically pure diethyl (1S,2R)-, (1S,2S)-, (1R,2R)- and (1R,2S)-2,3-di(tert-butoxycarbonyl)amino-1-hydroxypropylphosphonates were synthesised from diethyl (1S,2R,1'S)-, (1S,2S,1'R)-, (1R,2R,1'S)- and (1R,2S,1'R)-[N-(1-phenylethyl)]-2,3-epimino-1-hydroxypropylphosphonates, respectively, via aziridine ring opening with neat TMSN3 followed by hydrogenolysis in the presence of BoC(2)O. A plausible mechanism for the aziridine ring opening in 2,3-epimino-1-hydroxypropylphosphonates involving the intermediate aziridinium ions was proposed. Significant differences in the rates of the aziridine ring opening between diastereoisomeric phosphonates (1S,2R,1'S) and (1S,2S,1'R) were rationalised taking into account different conformations of the 1-phenylethyl group in both diastereoisomers. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.032
• 作为产物：
  描述：

  (S)-1-[(R)-α-甲基苄基]氮杂环丙烷-2-甲醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 反应 73.0h， 生成 diethyl (S)-hydroxy {(S)-1-[(R)-1-phenylethyl]aziridin-2-yl}methylphosphonate
  参考文献：
  名称：

  Synthesis of four enantiomers of 2-acetamido-1-hydroxypropylphosphonates

  摘要：

  Enantiomerically pure diethyl 2-acetamido-1-hydroxypropylphosphonates were synthesised from N-[(R)-(1-phenylethyl)]aziridine-(2S)- and N-[(S)-(1-phenylethyl)]aziridine-(2R)-carboxaldehydes via phosphonylation followed by acetylation of the hydroxy groups and the simultaneous hydrogenolytic cleavage of the aziridine rings and the removal of the chiral auxiliaries. In addition, enantiomerically pure diethyl (1S,2R)- and (1R,2S)-2-amino-1-hydroxypropylphosphonates (the phosphonate analogues of isothreonine) were separated. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.021