1,6,17,29-tetrakis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22,28-pentaazaoctacosane | 284666-64-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6,17,29-tetrakis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22,28-pentaazaoctacosane
• 英文别名: N'-[5-[[4-oxo-4-[phenylmethoxy(5-phenylmethoxypentyl)amino]butanoyl]amino]pentyl]-N'-phenylmethoxy-N-[5-(phenylmethoxyamino)pentyl]butanediamide
• CAS: 284666-64-4
• 化学式: C₅₁H₆₉N₅O₈
• 分子量: 880.138
• InChiKey: OZIANMYPWBIJPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  64
• 可旋转键数：
  35
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,6,17,29-tetrakis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22,28-pentaazaoctacosane 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 Desferri-danoxamin
  参考文献：
  名称：

  Total Synthesis of the Siderophore Danoxamine

  摘要：

  The total synthesis of the linear trihydroxamate siderophore, Danoxamine, is described. Danoxamine is a siderophore component of the naturally occurring siderophore-drug conjugates Salmycin A-D. The synthesis of Danoxamine features a series of coupling reactions involving N-(5-benzyloxypentyl)-O-benzylhydroxylamine being linked by a succinoyl linker to N-(benzyloxy)-1,5-pentanediamine. Two more succinoyl linkers and another N-(benzyloxy)-1,5-pentanediamine were used in coupling reactions to afford the fully protected siderophore. The linear tetrabenzyl-protected trihydroxamate was deprotected to afford the natural product Danoxamine.

  DOI：

  10.1021/jo000050m
• 作为产物：
  描述：

  5-氯戊腈 在 镍 二苯基磷酸 、 氨 、 氢气 、 sodium hydride 、 三乙胺 、 三氟乙酸 、 sodium iodide 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.58h， 生成 1,6,17,29-tetrakis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22,28-pentaazaoctacosane
  参考文献：
  名称：

  Total Synthesis of the Siderophore Danoxamine

  摘要：

  The total synthesis of the linear trihydroxamate siderophore, Danoxamine, is described. Danoxamine is a siderophore component of the naturally occurring siderophore-drug conjugates Salmycin A-D. The synthesis of Danoxamine features a series of coupling reactions involving N-(5-benzyloxypentyl)-O-benzylhydroxylamine being linked by a succinoyl linker to N-(benzyloxy)-1,5-pentanediamine. Two more succinoyl linkers and another N-(benzyloxy)-1,5-pentanediamine were used in coupling reactions to afford the fully protected siderophore. The linear tetrabenzyl-protected trihydroxamate was deprotected to afford the natural product Danoxamine.

  DOI：

  10.1021/jo000050m

文献信息

• Total Synthesis of Desferrisalmycin B
  作者：Li Dong、John M. Roosenberg、Marvin J. Miller

  DOI：10.1021/ja028386w

  日期：2002.12.1

  The first total synthesis of a naturally occurring siderophore antibiotic, desferrisalmycin B, is described, and the configuration of the unknown stereocenter is assigned. The synthesis features a synthetic strategy of constructing the novel amino-heptopyranoside component by stereoselective dihydroxylation followed by a Bose-modified Mitsunobu reaction. Through this convergent approach, other members of salmycins should also be synthetically accessible.
• Iron(III)-Templated Macrolactonization of Trihydroxamate Siderophores
  作者：Timothy A. Wencewicz、Allen G. Oliver、Marvin J. Miller

  DOI：10.1021/ol301869x

  日期：2012.9.7

  A method was developed to synthesize macrocyclic trihydroxamate siderophores using optimized Yamaguchi macrolactonization conditions. The natural ability of siderophores to bind iron(III) was exploited to template the reactions and allowed for rapid reaction rates, high product conversions, and the formation of large macrolactone rings up to 35 atoms. An X-ray structure of a 33-membered macrolactone siderophore-Fe(III) complex is presented.
• Total Synthesis of the Siderophore Danoxamine
  作者：John M. Roosenberg、Marvin J. Miller

  DOI：10.1021/jo000050m

  日期：2000.8.1

  The total synthesis of the linear trihydroxamate siderophore, Danoxamine, is described. Danoxamine is a siderophore component of the naturally occurring siderophore-drug conjugates Salmycin A-D. The synthesis of Danoxamine features a series of coupling reactions involving N-(5-benzyloxypentyl)-O-benzylhydroxylamine being linked by a succinoyl linker to N-(benzyloxy)-1,5-pentanediamine. Two more succinoyl linkers and another N-(benzyloxy)-1,5-pentanediamine were used in coupling reactions to afford the fully protected siderophore. The linear tetrabenzyl-protected trihydroxamate was deprotected to afford the natural product Danoxamine.