tert-butyl (2S,3R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-2-cyano-5-methylpyrrolidine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2S,3R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-2-cyano-5-methylpyrrolidine-1-carboxylate
• 化学式: C₁₇H₃₂N₂O₃Si
• 分子量: 340.538
• InChiKey: KREVPELGXYWCRK-HZSPNIEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester 在 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 生成 tert-butyl (2S,3R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-2-cyano-5-methylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Diastereoselective syntheses of (2R,3R,5R)- and (2S,3S,5S)-3-hydroxy-5-methyl-2-pyrrolidinecarboxylic acid as a component of actinomycin Z1

  摘要：

  A novel diastereoselective syntheses of both (2R,3R,5R)-1 and its enantiomer (7S,3S,5S)-1 were accomplished by employing trans-selective nucleophilic addition of cyanide to 3-benzoyloxy-N-acyliminium ions as the key step, starting from trans-4-hydroxy-L-proline. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00604-8

文献信息

• Diastereoselective syntheses of (2R,3R,5R)- and (2S,3S,5S)-3-hydroxy-5-methyl-2-pyrrolidinecarboxylic acid as a component of actinomycin Z1
  作者：Ken-ichi Tanaka、Hiroyuki Sawanishi

  DOI：10.1016/s0040-4020(98)00604-8

  日期：1998.8

  A novel diastereoselective syntheses of both (2R,3R,5R)-1 and its enantiomer (7S,3S,5S)-1 were accomplished by employing trans-selective nucleophilic addition of cyanide to 3-benzoyloxy-N-acyliminium ions as the key step, starting from trans-4-hydroxy-L-proline. (C) 1998 Elsevier Science Ltd. All rights reserved.

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