N-benzyloxycarbonyl-L-phenylalanyl-(N-(4-methoxybenzyl)-α,α-diisobutyl)glycine cyclohexylamide | 655239-33-1

• 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: N-benzyloxycarbonyl-L-phenylalanyl-(N-(4-methoxybenzyl)-α,α-diisobutyl)glycine cyclohexylamide
• CAS: 655239-33-1
• 化学式: C₄₁H₅₅N₃O₅
• 分子量: 669.905
• InChiKey: NVLREJGYNAOMLL-QNGWXLTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  49.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  96.97
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-L-phenylalanyl-(N-(4-methoxybenzyl)-α,α-diisobutyl)glycine cyclohexylamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以83.5%的产率得到(N-benzyloxycarbonyl-L-phenylalanyl)-α,α-diisobutylglycine
  参考文献：
  名称：

  Straightforward, racemization-free synthesis of peptides with fairly to very bulky di- and trisubstituted glycines

  摘要：

  Several fully protected tri- and pentapeptides containing a central symmetrical alpha,alpha-dialkyl glycine residue, with the alkyl group varying from methyl or ethyl to benzyl, were synthesized in good yields by a strategy based on the Ugi-Passerini reaction. Each Ugi-Passerini adduct was selectively cleaved and the product submitted to an assisted N,N'-dicyclohehylcarbodiimide coupling to an amino acid or dipeptide ester, respectively. Tripeptides as the above but containing a 4-methoxybenzyl group at the nitrogen atom of the central residue were also synthesized in fair to good yields by N-[(1H-benzotriazol-1-yl)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide assisted couplings. The results reported here show that our strategy is appropriate for routine synthesis of peptides incorporating these moieties. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.022
• 作为产物：
  描述：

  异氰环已烷 、 二异丁基酮 、 N-苄氧羰基-L-苯丙氨酸 、 4-甲氧基苄胺 反应 504.0h， 以70.1%的产率得到N-benzyloxycarbonyl-L-phenylalanyl-(N-(4-methoxybenzyl)-α,α-diisobutyl)glycine cyclohexylamide
  参考文献：
  名称：

  Straightforward, racemization-free synthesis of peptides with fairly to very bulky di- and trisubstituted glycines

  摘要：

  Several fully protected tri- and pentapeptides containing a central symmetrical alpha,alpha-dialkyl glycine residue, with the alkyl group varying from methyl or ethyl to benzyl, were synthesized in good yields by a strategy based on the Ugi-Passerini reaction. Each Ugi-Passerini adduct was selectively cleaved and the product submitted to an assisted N,N'-dicyclohehylcarbodiimide coupling to an amino acid or dipeptide ester, respectively. Tripeptides as the above but containing a 4-methoxybenzyl group at the nitrogen atom of the central residue were also synthesized in fair to good yields by N-[(1H-benzotriazol-1-yl)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide assisted couplings. The results reported here show that our strategy is appropriate for routine synthesis of peptides incorporating these moieties. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.022