cis-2-tosyloxymethyl-3-trityloxymethyloxirane | 1415988-53-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: cis-2-tosyloxymethyl-3-trityloxymethyloxirane
• 英文别名: 2-tosyloxymethyl-3-trityloxymethyloxirane
• CAS: 1415988-53-2
• 化学式: C₃₀H₂₈O₅S
• 分子量: 500.615
• InChiKey: IMSGJGCWUNPSJS-URLMMPGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.13
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  cis-2-tosyloxymethyl-3-trityloxymethyloxirane 在 正丁基锂 、 potassium tert-butylate 、 二异丙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 170.0h， 生成 (+)-(1'R,2R,3R)-3-(1-hydroxy-2-trityloxyethyl)-2-phenyl-1-methylazetidine
  参考文献：
  名称：

  Novel stereoselective synthesis of 1,2,3-trisubstituted azetidines

  摘要：

  A novel, superbase induced diastereoselective transformation of benzylamino groups containing oxiranes has provided a series of trans-1,2,3-trisubstituted azetidines in good yields. The reaction of the corresponding optically active cis-2,3-disubstituted oxirane yielded the azetidine derivative as a single enantiomer. The structures of the new azetidines were confirmed by NMR spectroscopic methods and, in one case, by single crystal diffraction measurements. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.014
• 作为产物：
  描述：

  ((2R,3S)-3-((trityloxy)methyl)oxiran-2-yl)methanol 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 24.0h， 以91%的产率得到cis-2-tosyloxymethyl-3-trityloxymethyloxirane
  参考文献：
  名称：

  Novel stereoselective synthesis of 1,2,3-trisubstituted azetidines

  摘要：

  A novel, superbase induced diastereoselective transformation of benzylamino groups containing oxiranes has provided a series of trans-1,2,3-trisubstituted azetidines in good yields. The reaction of the corresponding optically active cis-2,3-disubstituted oxirane yielded the azetidine derivative as a single enantiomer. The structures of the new azetidines were confirmed by NMR spectroscopic methods and, in one case, by single crystal diffraction measurements. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.014