tert-butyl (S)-4-(benzyloxycarbonylamino)-3-[(1R,3R)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]butanoate | 1138793-50-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (S)-4-(benzyloxycarbonylamino)-3-[(1R,3R)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]butanoate
• 英文别名: tert-butyl (3S)-3-[(1R,3R)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]-4-(phenylmethoxycarbonylamino)butanoate
• CAS: 1138793-50-6
• 化学式: C₂₆H₃₉NO₆
• 分子量: 461.599
• InChiKey: FVRAUGZZPNZGSO-NJDAHSKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-4-(benzyloxycarbonylamino)-3-[(1R,3R)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]butanoate 在 4-甲基苯磺酸吡啶 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以97%的产率得到tert-butyl (S)-3-[(1R,3R)-3-acetyl-2,2-dimethylcyclobutyl]-4-(benzyloxy-carbonylamino)butanoate
  参考文献：
  名称：

  Stereoselective synthesis of cyclobutyl γ-amino acids leading to branched peptides with a cyclobutane core

  摘要：

  Alternative synthetic routes are provided to synthesize gamma-amino acids in their free form or conveniently protected for their selective incorporation into ramified gamma-peptides with a cyclobutane core. The key synthetic-step involves the stereoselective conjugate addition of nitromethane to chiral cyclobutyl alkenoates prepared from (-)-verbenone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.019
• 作为产物：
  描述：

  tert-butyl (S)-4-(4-(tert-butoxycarbonylamino)butanoylamino)-3-[(1R,3R)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)-cyclobutyl]butanoate 、 氯甲酸苄酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以70%的产率得到tert-butyl (S)-4-(benzyloxycarbonylamino)-3-[(1R,3R)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]butanoate
  参考文献：
  名称：

  Stereoselective synthesis of cyclobutyl γ-amino acids leading to branched peptides with a cyclobutane core

  摘要：

  Alternative synthetic routes are provided to synthesize gamma-amino acids in their free form or conveniently protected for their selective incorporation into ramified gamma-peptides with a cyclobutane core. The key synthetic-step involves the stereoselective conjugate addition of nitromethane to chiral cyclobutyl alkenoates prepared from (-)-verbenone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.019