diethyl (2R,3S)-3-acetoxymethyl-1-(tert-butoxycarbonyl)aziridin-2-yl-2-phosphonate | 1284299-43-9

• 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,3S)-3-acetoxymethyl-1-(tert-butoxycarbonyl)aziridin-2-yl-2-phosphonate
• 英文别名: tert-butyl (2S,3R)-2-(acetyloxymethyl)-3-[diethoxy(oxido)phosphaniumyl]aziridine-1-carboxylate
• CAS: 1284299-43-9
• 化学式: C₁₄H₂₆NO₇P
• 分子量: 351.337
• InChiKey: GWBWDGLXRFHFRW-VPUIJTBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  97.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  diethyl (1S,2S)-3-acetoxy-1-hydroxy-2-[(R)-1-phenylethylamino]propylphosphonate 在 palladium 10% on activated carbon 、 氢气 、 甲基磺酰氯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， -70.0~20.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 diethyl (2R,3S)-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