(3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester | 213699-27-5

• 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: (3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS: 213699-27-5
• 化学式: C₁₆H₃₃NO₄Si
• 分子量: 331.528
• InChiKey: ZFTDGONHOXVSOB-ZNRZSNADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  tert-butyl (2R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-methylpyrrolidine-1-carboxylate 在 ruthenium(IV) oxide 、 sodium periodate 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 3.5h， 生成 (3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester
  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