(2S,11S,20S)-2,6-cyclo-11,15-cyclo-20,24-cyclo-26-(benzyloxycarbonylamino)-6,9,15,18,24-pentaaza-10,19-dioxohexacosanoic acid methyl ester | 350028-10-3

• 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: (2S,11S,20S)-2,6-cyclo-11,15-cyclo-20,24-cyclo-26-(benzyloxycarbonylamino)-6,9,15,18,24-pentaaza-10,19-dioxohexacosanoic acid methyl ester
• CAS: 350028-10-3
• 化学式: C₃₀H₄₆N₆O₆
• 分子量: 586.732
• InChiKey: NJARLCQNEMUKEO-GSDHBNRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  132.55
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,11S,20S)-2,6-cyclo-11,15-cyclo-20,24-cyclo-26-(benzyloxycarbonylamino)-6,9,15,18,24-pentaaza-10,19-dioxohexacosanoic acid methyl ester 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 720.0h， 生成 (6S,15S,24S)-1,4,10,13,19,22-hexaazatetracyclo[22.3.0.0^6,10.0^15,19]heptacosane-5,14,23-trione
  参考文献：
  名称：

  The synthesis of l-proline derived hexaazamacrocyclic ligands of C3 symmetry via intramolecular methyl ester aminolysis

  摘要：

  A convenient synthesis of enantiomerically pure 18-, 21-. and 24-membered hexaaza-crown ligands is presented. Linear alpha,omega -aminoesters, prepared from L-proline, undergo intramolecular aminolysis to afford the corresponding 18-, 21-, and 24-membered macrocyclic amides in satisfactory yields (42, 65. and 22%, respectively). These were subsequently transformed into the title macrocyclic hexamines via exhaustive reduction with a borane-dimethylsulfide complex. X-Ray structures of two larger macrocyclic amides are also presented. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00068-4
• 作为产物：
  描述：

  (2S)-N-(N'-(benzyloxycarbonyl)-2'-aminoethyl)-proline 、 methyl (2S)-1-[2-[[(2S)-1-(2-aminoethyl)pyrrolidine-2-carbonyl]amino]ethyl]pyrrolidine-2-carboxylate 在 三乙胺 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到(2S,11S,20S)-2,6-cyclo-11,15-cyclo-20,24-cyclo-26-(benzyloxycarbonylamino)-6,9,15,18,24-pentaaza-10,19-dioxohexacosanoic acid methyl ester
  参考文献：
  名称：

  The synthesis of l-proline derived hexaazamacrocyclic ligands of C3 symmetry via intramolecular methyl ester aminolysis

  摘要：

  A convenient synthesis of enantiomerically pure 18-, 21-. and 24-membered hexaaza-crown ligands is presented. Linear alpha,omega -aminoesters, prepared from L-proline, undergo intramolecular aminolysis to afford the corresponding 18-, 21-, and 24-membered macrocyclic amides in satisfactory yields (42, 65. and 22%, respectively). These were subsequently transformed into the title macrocyclic hexamines via exhaustive reduction with a borane-dimethylsulfide complex. X-Ray structures of two larger macrocyclic amides are also presented. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00068-4