tert-butyl 4-[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-4-methylpentan-2-yl]-3-oxopiperazine-1-carboxylate | 186820-92-8

• 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 4-[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-4-methylpentan-2-yl]-3-oxopiperazine-1-carboxylate
• CAS: 186820-92-8
• 化学式: C₂₁H₄₂N₂O₄Si
• 分子量: 414.661
• InChiKey: WLLHFJDNIYPAST-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-4-methylpentan-2-yl]-3-oxopiperazine-1-carboxylate 在 jones reagent 、 四丁基氟化铵 、 叔丁基锂 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 4.67h， 生成 (2S,3'S)-2-isobutyl-2-[4'-(tert-butoxycarbonyl)-3'-isobutyl-2'-oxopiperazin-1'-yl]acetic acid
  参考文献：
  名称：

  Efficient Synthesis of Conformationally Constrained Peptidomimetics Containing 2-Oxopiperazines¹

  摘要：

  The enantioselective synthesis of a series of peptides containing the 3-substituted 2-oxopiperazine system is reported. The method involves a direct diastereoselective alkylation of the N-(hydroxyalkyl)-2-oxopiperazine 3, prepared in three steps from methyl L-leucinate in 38% yield, followed by oxidation of the hydroxyl function. Esterification of the resulting acids 11 and then deprotection and acylation of N-4 afforded tripeptide analogues 16 substituted by a large variety of alkyl side chains at the 2-position of the 2-oxopiperazine.

  DOI：

  10.1021/jo961398d
• 作为产物：
  描述：

  Boc-Gly-ψ(CH2NH)-Leu-OMe 在 N-甲基吗啉 、 咪唑 、 lithium aluminium tetrahydride 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.25h， 生成 tert-butyl 4-[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-4-methylpentan-2-yl]-3-oxopiperazine-1-carboxylate
  参考文献：
  名称：

  Efficient Synthesis of Conformationally Constrained Peptidomimetics Containing 2-Oxopiperazines¹

  摘要：

  The enantioselective synthesis of a series of peptides containing the 3-substituted 2-oxopiperazine system is reported. The method involves a direct diastereoselective alkylation of the N-(hydroxyalkyl)-2-oxopiperazine 3, prepared in three steps from methyl L-leucinate in 38% yield, followed by oxidation of the hydroxyl function. Esterification of the resulting acids 11 and then deprotection and acylation of N-4 afforded tripeptide analogues 16 substituted by a large variety of alkyl side chains at the 2-position of the 2-oxopiperazine.

  DOI：

  10.1021/jo961398d

文献信息

• Efficient Synthesis of Conformationally Constrained Peptidomimetics Containing 2-Oxopiperazines¹
  作者：Adriana Pohlmann、Vincent Schanen、Dominique Guillaume、Jean-Charles Quirion、Henri-Philippe Husson

  DOI：10.1021/jo961398d

  日期：1997.2.1

  The enantioselective synthesis of a series of peptides containing the 3-substituted 2-oxopiperazine system is reported. The method involves a direct diastereoselective alkylation of the N-(hydroxyalkyl)-2-oxopiperazine 3, prepared in three steps from methyl L-leucinate in 38% yield, followed by oxidation of the hydroxyl function. Esterification of the resulting acids 11 and then deprotection and acylation of N-4 afforded tripeptide analogues 16 substituted by a large variety of alkyl side chains at the 2-position of the 2-oxopiperazine.