[3-((S)-2-Acetylamino-propionylamino)-3-benzyl-2-oxo-azetidin-1-yl]-methyl-carbamic acid benzyl ester | 869190-18-1

• 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: [3-((S)-2-Acetylamino-propionylamino)-3-benzyl-2-oxo-azetidin-1-yl]-methyl-carbamic acid benzyl ester
• CAS: 869190-18-1
• 化学式: C₂₄H₂₈N₄O₅
• 分子量: 452.51
• InChiKey: HVCCBUMXZPSSBZ-KEJDIYNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  108.05
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [3-((S)-2-Acetylamino-propionylamino)-3-benzyl-2-oxo-azetidin-1-yl]-methyl-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以95%的产率得到(S)-2-Acetylamino-N-(3-benzyl-1-methylamino-2-oxo-azetidin-3-yl)-propionamide
  参考文献：
  名称：

  A general strategy for the synthesis of azapeptidomimetic lactams

  摘要：

  A selection of azapeptidomimetics containing constraining lactam rings have been prepared by Mitsunobu cyclization of serine/ homologated serine-azaalanine derivatives. These include sterically-congested beta-lactams, as well as gamma-butyrolactam and delta-valerolactam analogs. A novel azaamino acid acylation method was developed to prepare the sterically demanding alpha-benzyl-serine-azaalanine precursor. In all cases, the Mitsunobu conditions were highly efficient in forming the desired azapeptidomimetic lactams. The reported process represents a general strategy for the synthesis of peptidomimetic structures with a constraining lactam ring. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.029
• 作为产物：
  描述：

  L-苯丙氨酸乙酯盐酸盐 在 盐酸 、 lithium hydroxide 、 正丁基锂 、 三甲基铝 、 碳酸氢钠 、 magnesium sulfate 、 三乙胺 、 二异丙胺 、 三苯基膦 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 11.0h， 生成 [3-((S)-2-Acetylamino-propionylamino)-3-benzyl-2-oxo-azetidin-1-yl]-methyl-carbamic acid benzyl ester
  参考文献：
  名称：

  A general strategy for the synthesis of azapeptidomimetic lactams

  摘要：

  A selection of azapeptidomimetics containing constraining lactam rings have been prepared by Mitsunobu cyclization of serine/ homologated serine-azaalanine derivatives. These include sterically-congested beta-lactams, as well as gamma-butyrolactam and delta-valerolactam analogs. A novel azaamino acid acylation method was developed to prepare the sterically demanding alpha-benzyl-serine-azaalanine precursor. In all cases, the Mitsunobu conditions were highly efficient in forming the desired azapeptidomimetic lactams. The reported process represents a general strategy for the synthesis of peptidomimetic structures with a constraining lactam ring. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.029