tert-butyl 4-[(2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(2R)-2-(oxan-2-yloxy)-4-(phenylmethoxycarbonylamino)butyl]-phenylmethoxycarbonylamino]hexanoyl]amino]-3-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-3-oxopropyl]imidazole-1-carboxylate | 189280-55-5

• 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)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(2R)-2-(oxan-2-yloxy)-4-(phenylmethoxycarbonylamino)butyl]-phenylmethoxycarbonylamino]hexanoyl]amino]-3-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-3-oxopropyl]imidazole-1-carboxylate
• CAS: 189280-55-5
• 化学式: C₆₃H₇₉N₇O₁₄
• 分子量: 1158.36
• InChiKey: CKOSCJROGMSVCG-CDUJDUMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  84
• 可旋转键数：
  33
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  253
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[(2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(2R)-2-(oxan-2-yloxy)-4-(phenylmethoxycarbonylamino)butyl]-phenylmethoxycarbonylamino]hexanoyl]amino]-3-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-3-oxopropyl]imidazole-1-carboxylate 在 4-氨甲基哌啶 作用下， 以 氯仿 为溶剂， 反应 2.67h， 以68%的产率得到4-[(S)-2-((S)-2-Amino-6-{benzyloxycarbonyl-[(R)-4-benzyloxycarbonylamino-2-(tetrahydro-pyran-2-yloxy)-butyl]-amino}-hexanoylamino)-2-(tert-butoxycarbonylmethyl-carbamoyl)-ethyl]-imidazole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Development of a Hypusine Reagent for Peptide Synthesis

  摘要：

  The synthesis of a reagent that enables the incorporation of the unusual amino acid (2S,9R)hypusine (Hpu) into peptide sequences is described. The reagent, (2S,SR)-11-[(benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2- [(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)- 7-azaundecanoic acid, is utilized in the synthesis of a hexapeptide containing the primary pentapeptide sequence of the eukaryotic initiation factor eIF-5A, L-Cys-L-Thr-Gly-Hpu-L-His-Gly. The reagent is shown to be effective for both solution phase and Merrifield resin synthesis.

  DOI：

  10.1021/jo970119z
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 palladium on activated charcoal 盐酸 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.83h， 生成 tert-butyl 4-[(2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(2R)-2-(oxan-2-yloxy)-4-(phenylmethoxycarbonylamino)butyl]-phenylmethoxycarbonylamino]hexanoyl]amino]-3-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-3-oxopropyl]imidazole-1-carboxylate
  参考文献：
  名称：

  Development of a Hypusine Reagent for Peptide Synthesis

  摘要：

  The synthesis of a reagent that enables the incorporation of the unusual amino acid (2S,9R)hypusine (Hpu) into peptide sequences is described. The reagent, (2S,SR)-11-[(benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2- [(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)- 7-azaundecanoic acid, is utilized in the synthesis of a hexapeptide containing the primary pentapeptide sequence of the eukaryotic initiation factor eIF-5A, L-Cys-L-Thr-Gly-Hpu-L-His-Gly. The reagent is shown to be effective for both solution phase and Merrifield resin synthesis.

  DOI：

  10.1021/jo970119z