α-azido-N-(tert-butoxycarbonyl)glycine methyl ester | 160380-86-9

• 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: α-azido-N-(tert-butoxycarbonyl)glycine methyl ester
• 英文别名: methyl 2-azido-2-((tert-butoxycarbonyl)amino)acetate；Methyl 2-azido-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate；methyl 2-azido-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 160380-86-9
• 化学式: C₈H₁₄N₄O₄
• 分子量: 230.224
• InChiKey: HBMFKLJCUAAJMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α-azido-N-(tert-butoxycarbonyl)glycine methyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、300.0 kPa 条件下， 反应 17.0h， 生成 α-(tert-butyloxycarbonylamino)-N^α-(benzyloxycarbonyl)glycine methyl ester
  参考文献：
  名称：

  Synthesis of Differently Protected α-Aminoglycines and Their Peptide Derivatives

  摘要：

  受相容保护的α-氨基甘氨酸及其含有该成分的二肽和三肽，是经由相应的α-羟基甘氨酸制备的。

  DOI：

  10.1055/s-1994-25592
• 作为产物：
  描述：

  BOC-甘氨酸甲酯 在 2-碘苯甲酸 、 叠氮基三甲基硅烷 、 间氯过氧苯甲酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以34%的产率得到α-azido-N-(tert-butoxycarbonyl)glycine methyl ester
  参考文献：
  名称：

  N ‐Terminal Selective C−H Azidation of Proline‐Containing Peptides: a Platform for Late‐Stage Diversification

  摘要：

  AbstractA methodology for the C−H azidation of N‐terminal proline‐containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at the carbamate‐protected N‐terminal residue in presence of the numerous other functional groups present on the molecules. Post‐functionalizations of the obtained aminal compounds were achieved: cycloaddition reactions or C−C bond formations via a sequence of imine formation/nucleophilic addition were performed, offering an easy access to diversified peptides.

  DOI：

  10.1002/chem.202200368

文献信息

• Synthesis of Differently Protected α-Aminoglycines and Their Peptide Derivatives
  作者：Ulrich Schmidt、Florian Stäbler、Albrecht Lieberknecht

  DOI：10.1055/s-1994-25592

  日期：——

  Compatibly protected α-aminoglycine and di- and tripeptides containing it are prepared from the corresponding α-hydroxyglycines.

  受相容保护的α-氨基甘氨酸及其含有该成分的二肽和三肽，是经由相应的α-羟基甘氨酸制备的。
• <i>N</i> ‐Terminal Selective C−H Azidation of Proline‐Containing Peptides: a Platform for Late‐Stage Diversification
  作者：Emmanuelle M. D. Allouche、Raphaël Simonet‐Davin、Jerome Waser

  DOI：10.1002/chem.202200368

  日期：2022.3.22

  AbstractA methodology for the C−H azidation of N‐terminal proline‐containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at the carbamate‐protected N‐terminal residue in presence of the numerous other functional groups present on the molecules. Post‐functionalizations of the obtained aminal compounds were achieved: cycloaddition reactions or C−C bond formations via a sequence of imine formation/nucleophilic addition were performed, offering an easy access to diversified peptides.