(3S,5S)-1-benzyl-3-(ethoxycarbonylmethyl)-4-tert-butoxycarbonyl-5-methyl-2-oxopiperazine | 1004286-99-0

• 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: (3S,5S)-1-benzyl-3-(ethoxycarbonylmethyl)-4-tert-butoxycarbonyl-5-methyl-2-oxopiperazine
• 英文别名: tert-butyl (2S,6S)-4-benzyl-2-(2-ethoxy-2-oxoethyl)-6-methyl-3-oxopiperazine-1-carboxylate
• CAS: 1004286-99-0
• 化学式: C₂₁H₃₀N₂O₅
• 分子量: 390.48
• InChiKey: LOVRASNRPFPMTM-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-1-benzyl-4-tert-butoxycarbonyl-5-methyl-2-oxopiperazine 、 溴乙酸乙酯 在 六甲基磷酰三胺 、 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 3.25h， 以40%的产率得到(3S,5S)-1-benzyl-3-(ethoxycarbonylmethyl)-4-tert-butoxycarbonyl-5-methyl-2-oxopiperazine
  参考文献：
  名称：

  A new versatile and diastereoselective synthesis of polysubstituted 2-oxopiperazines from naturally occurring amino acids

  摘要：

  A highly stereoselective approach to 1,3,4,5- and 1,3,3',4,5-polysubstituted 2-oxopiperazines is reported. The method is based on the synthetic elaboration of naturally occurring amino acids to obtain enantiomerically enriched C-5 substituted oxopiperazines, which are further functionalized at C-3 via enolate formation and reaction with electrophiles. Notably, the two nitrogens of the ring can be orthogonally protected. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.027

文献信息

• A new versatile and diastereoselective synthesis of polysubstituted 2-oxopiperazines from naturally occurring amino acids
  作者：Gianna Reginato、Barbara Di Credico、Daniele Andreotti、Anna Mingardi、Alfredo Paio、Daniele Donati

  DOI：10.1016/j.tetasy.2007.10.027

  日期：2007.11

  A highly stereoselective approach to 1,3,4,5- and 1,3,3',4,5-polysubstituted 2-oxopiperazines is reported. The method is based on the synthetic elaboration of naturally occurring amino acids to obtain enantiomerically enriched C-5 substituted oxopiperazines, which are further functionalized at C-3 via enolate formation and reaction with electrophiles. Notably, the two nitrogens of the ring can be orthogonally protected. (c) 2007 Elsevier Ltd. All rights reserved.