1,6,17-tris(benzyloxy)-7,10-dioxo-6,11,17-triazaheptadecane | 284666-62-2

• 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-tris(benzyloxy)-7,10-dioxo-6,11,17-triazaheptadecane
• 英文别名: N'-phenylmethoxy-N-[5-(phenylmethoxyamino)pentyl]-N'-(5-phenylmethoxypentyl)butanediamide
• CAS: 284666-62-2
• 化学式: C₃₅H₄₇N₃O₅
• 分子量: 589.775
• InChiKey: PQCFDXMDJIUNEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  43
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,6,17-tris(benzyloxy)-7,10-dioxo-6,11,17-triazaheptadecane 在 palladium on activated charcoal 4-二甲氨基吡啶 、 二苯基磷酸 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 31.33h， 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 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.25h， 生成 1,6,17-tris(benzyloxy)-7,10-dioxo-6,11,17-triazaheptadecane
  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 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.