1-(N-benzyloxycarbonyl-L-phenylalanylamino)cyclohexylcarboxylic acid | 215931-32-1

• 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: 1-(N-benzyloxycarbonyl-L-phenylalanylamino)cyclohexylcarboxylic acid
• 英文别名: 1-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]cyclohexane-1-carboxylic acid
• CAS: 215931-32-1
• 化学式: C₂₄H₂₈N₂O₅
• 分子量: 424.497
• InChiKey: MECHEGMXXQFZNC-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(N-benzyloxycarbonyl-L-phenylalanylamino)cyclohexylcarboxylic acid 、 甘氨酸叔丁酯 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以91.9%的产率得到1-(N-benzyloxycarbonyl-L-phenylalanylamino)cyclohexylcarbonylglycine tert-butyl ester
  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：

  1-[N-(N'-benzyloxycarbonyl-L-phenylalanyl)-N-(4-methoxybenzyl)amino]cyclohexylcarboxylic acid cyclohexylamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到1-(N-benzyloxycarbonyl-L-phenylalanylamino)cyclohexylcarboxylic acid
  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

文献信息

• Straightforward, racemization-free synthesis of peptides with fairly to very bulky di- and trisubstituted glycines
  作者：Filipa C.S.C. Pinto、Sílvia M.M.A. Pereira-Lima、Hernâni L.S. Maia

  DOI：10.1016/j.tet.2009.09.022

  日期：2009.11

  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.