1-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl)cyclohexyl benzoyl-D-valinate | 1072013-94-5

• 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: 1-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl)cyclohexyl benzoyl-D-valinate
• CAS: 1072013-94-5
• 化学式: C₂₉H₃₆N₂O₆
• 分子量: 508.615
• InChiKey: OUMGAQXHSKCQOR-BJKOFHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  110.8
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  D-N-苯甲酰缬氨酸 、 环己酮 、 methyl (R)-(+)-2-isocyano-3-phenylpropionate 反应 35.0h， 生成 1-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl)cyclohexyl benzoyl-D-valinate 、 1-(((R)-1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl)cyclohexyl benzoyl-D-valinate
  参考文献：
  名称：

  α-Amino acids as acid components in the Passerini reaction: influence of N-protection on the yield and stereoselectivity

  摘要：

  The Passerini reaction offers an easy access to depsipeptides, when both acid and isocyanide are derived from of.-amino acids. However, racemisation of isocyanides derived from alpha-amino acid esters severely limits their use in the Passerini reaction. In order to overcome this limitation, a study on the influence of the alpha-amino acid N-protecting group on the yield and diastereoisomeric ratio of the product of the Passerini reaction was performed. Six different protecting groups were tested. Their influence turns out to be crucial and is not constant when the amino acid is changed. After optimisation, the Passerini reaction products with cyclohexanone as the carbonyl component were obtained with 99% yield and >98% de. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.064