diethyl (2R,3R)-3-acetoxymethyl-1-[(S)-1-phenylethyl]aziridin-2-yl-2-phosphonate | 1284299-42-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl (2R,3R)-3-acetoxymethyl-1-[(S)-1-phenylethyl]aziridin-2-yl-2-phosphonate
• CAS: 1284299-42-8
• 化学式: C₁₇H₂₆NO₅P
• 分子量: 355.371
• InChiKey: NUYZQCUXEIZOFC-QKARTMHWSA-N

物化性质

• 沸点：
  428.1±38.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 diethyl (2R,3R)-3-acetoxymethyl-1-[(S)-1-phenylethyl]aziridin-2-yl-2-phosphonate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 以86%的产率得到diethyl (2R,3R)-3-acetoxymethyl-1-(tert-butoxycarbonyl)aziridin-2-yl-2-phosphonate
  参考文献：
  名称：

  Synthesis of four stereoisomers of protected 1,2-epiimino-3-hydroxypropylphosphonates

  摘要：

  Enantiomerically pure protected 1,2-epiimino-3-hydroxypropylphosphonates were synthesised from hydroxy-1-{[(R)- or (S)-1-phenylethyl]aziridin-2-yl}methylphosphonates via regioselective ring opening with acetic acid followed by a stereospecific intramolecular cyclisation of 3-acetoxy-1-mesyloxy-2-(1-phenylethyl)aminopropylphosphonates and hydrogenolytic removal of the 1-phenylethyl group in the presence of Boc(2)O. The trans-isomers of 3-acetoxy-[N-(1-phenylethyl)-1,2-epiimino]propylphosphonates exist as a 2:1 mixture of invertomers, which were fully structurally characterised based on their (1)H and (13)C NMR spectroscopic data. Large differences in the (1)J(C-P) values in N-(1-phenylethyl)aziridine-2-phosphonates were noticed depending on the spatial arrangement of the nitrogen lone pair and the phosphorus atom (syn-periplanar ca. 215 Hz; anti-periplanar-182 Hz). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.005