Boc-Met-ψ[CH2NC] | 1245908-98-8

• 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: Boc-Met-ψ[CH2NC]
• 英文别名: (S)-tert-butyl 1-isocyano-4-(methylthio)butan-2-ylcarbamate
• CAS: 1245908-98-8
• 化学式: C₁₁H₂₀N₂O₂S
• 分子量: 244.358
• InChiKey: LYICAZIBABMTIW-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  42.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Boc-Met-ψ[CH2NC] 在 selenium 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(S)-tert-butyl 1-isoselenocyanato-4-(methylthio)butan-2-ylcarbamate
  参考文献：
  名称：

  Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

  摘要：

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.082
• 作为产物：
  描述：

  (S)-tert-butyl 1-formamido-4-(methylthio)butan-2-ylcarbamate 在 伯吉斯试剂 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到Boc-Met-ψ[CH2NC]
  参考文献：
  名称：

  Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

  摘要：

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.082

文献信息

• Synthesis of novel glycopeptidomimetics via Nβ-protected-amino alkyl isonitrile based Ugi 4C reaction
  作者：Basavalingappa Vasantha、Girish Prabhu、Hosmani Basavaprabhu、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2013.06.013

  日期：2013.8

  The Ugi-4C reaction employing Nβ-protected-amino alkyl isonitrile, amino acid ester, aldehyde, and glycosyl acid has resulted in novel glycosylated peptidomimetics. The extension of MCR products for the synthesis of N,N′-orthogonally protected glycosylated peptidomimetics has also been demonstrated.

  采用的Ugi-4C反应Ñ β -保护的氨基烷基异腈，氨基酸酯，醛和糖基酸已导致新颖糖基化的肽模拟物。还已经证明了MCR产物用于合成N，N'-正交保护的糖基化肽模拟物的扩展。