diethyl (1S,2R)-3-azido-2-[(S)-1-phenylethyl]amino-1-trimethylsilyloxypropylphosphonate | 1202351-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl (1S,2R)-3-azido-2-[(S)-1-phenylethyl]amino-1-trimethylsilyloxypropylphosphonate
• CAS: 1202351-36-7
• 化学式: C₁₈H₃₃N₄O₄PSi
• 分子量: 428.544
• InChiKey: HVKUWLMASKUXFA-JQHSSLGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  28.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  105.55
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl (1S,2R)-3-azido-2-[(S)-1-phenylethyl]amino-1-trimethylsilyloxypropylphosphonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以59%的产率得到diethyl (1S,2R)-3-azido-2-[(S)-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：

  diethyl (S)-hydroxy{(R)-1-[(S)-1-phenylethyl]aziridin-2-yl}methylphosphonate 、 叠氮基三甲基硅烷 以 二氯甲烷 为溶剂， 反应 336.0h， 以31%的产率得到diethyl (1S,2R)-3-azido-2-[(S)-1-phenylethyl]amino-1-trimethylsilyloxypropylphosphonate
  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