methyl N⁵-acetyl-N⁵-benzyloxy-N²-(2,3-dibenzyloxybenzoyl)aminohexanoylcarbonyl-L-ornithinate | 1022160-14-0

• 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: methyl N⁵-acetyl-N⁵-benzyloxy-N²-(2,3-dibenzyloxybenzoyl)aminohexanoylcarbonyl-L-ornithinate
• 英文别名: methyl (2S)-5-[acetyl(phenylmethoxy)amino]-2-[6-[[2,3-bis(phenylmethoxy)benzoyl]amino]hexanoylamino]pentanoate
• CAS: 1022160-14-0
• 化学式: C₄₂H₄₉N₃O₈
• 分子量: 723.866
• InChiKey: BETUAHUFDWCMKB-QNGWXLTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  53
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl N⁵-acetyl-N⁵-benzyloxy-N²-(2,3-dibenzyloxybenzoyl)aminohexanoylcarbonyl-L-ornithinate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以92%的产率得到N⁵-acetyl-N⁵-benzyloxy-N²-(2,3-dibenzyloxybenzoyl)aminohexanoylcarbonyl-L-ornithine
  参考文献：
  名称：

  Design and synthesis of a novel protected mixed ligand siderophore

  摘要：

  A novel siderophore analog (4) has been designed to facilitate iron transport-mediated drug delivery and drug release. This mixed ligand siderophore analog includes three bidentate ligands intended to octahedrally coordinate iron (III). The ligands include a 2,3-dihydroxy benzoic acid moiety, N(5)-acetyl-N(5)-hydroxy-L-ornithine, and a beta-N-hydroxy-alpha,beta-diaminopropionic acid derivative. The total synthesis of 15, a form of 4 that is suitably protected, yet contains a free carboxylic acid for subsequent drug conjugation, is described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.007
• 作为产物：
  描述：

  methyl (2S)-5-[acetyl(phenylmethoxy)amino]-2-(phenylmethoxycarbonylamino)pentanoate 、 (2,3-dibenzyloxybenzoyl)aminohexanoic acid 在 氢溴酸 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 17.5h， 以91%的产率得到methyl N⁵-acetyl-N⁵-benzyloxy-N²-(2,3-dibenzyloxybenzoyl)aminohexanoylcarbonyl-L-ornithinate
  参考文献：
  名称：

  Design and synthesis of a novel protected mixed ligand siderophore

  摘要：

  A novel siderophore analog (4) has been designed to facilitate iron transport-mediated drug delivery and drug release. This mixed ligand siderophore analog includes three bidentate ligands intended to octahedrally coordinate iron (III). The ligands include a 2,3-dihydroxy benzoic acid moiety, N(5)-acetyl-N(5)-hydroxy-L-ornithine, and a beta-N-hydroxy-alpha,beta-diaminopropionic acid derivative. The total synthesis of 15, a form of 4 that is suitably protected, yet contains a free carboxylic acid for subsequent drug conjugation, is described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.007

文献信息

• Design and synthesis of a novel protected mixed ligand siderophore
  作者：Pingyu Ding、Clara E. Schous、Marvin J. Miller

  DOI：10.1016/j.tetlet.2008.02.007

  日期：2008.3

  A novel siderophore analog (4) has been designed to facilitate iron transport-mediated drug delivery and drug release. This mixed ligand siderophore analog includes three bidentate ligands intended to octahedrally coordinate iron (III). The ligands include a 2,3-dihydroxy benzoic acid moiety, N(5)-acetyl-N(5)-hydroxy-L-ornithine, and a beta-N-hydroxy-alpha,beta-diaminopropionic acid derivative. The total synthesis of 15, a form of 4 that is suitably protected, yet contains a free carboxylic acid for subsequent drug conjugation, is described. (C) 2008 Elsevier Ltd. All rights reserved.