6,17,28-tris(benzyloxy)-7,10,18,21,29-pentaoxo-6,11,17,22,28-pentaazatriacontanenitrile | 112139-65-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6,17,28-tris(benzyloxy)-7,10,18,21,29-pentaoxo-6,11,17,22,28-pentaazatriacontanenitrile
• 英文别名: N'-<5-<<4-<<5-pentyl>amino>-1,4-dioxobutyl>(phenylmethoxy)amino>pentyl>-N-(4-cyanobutyl)-N-(phenylmethoxy)butanediamide；N-<5-<3-<(4-cyanobutyl)(benzyloxy)carbamoyl>propionamido>pentyl>-3-<<5-<(benzyloxy)acetylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid；N-[5-[acetyl(phenylmethoxy)amino]pentyl]-N'-[5-[[4-[4-cyanobutyl(phenylmethoxy)amino]-4-oxobutanoyl]amino]pentyl]-N'-phenylmethoxybutanediamide
• CAS: 112139-65-8
• 化学式: C₄₆H₆₂N₆O₈
• 分子量: 827.034
• InChiKey: VWXFQLMSPIAWGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  60
• 可旋转键数：
  31
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  171
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6,17,28-tris(benzyloxy)-7,10,18,21,29-pentaoxo-6,11,17,22,28-pentaazatriacontanenitrile 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 7.5h， 以84%的产率得到N'-[5-[[4-[[5-(乙酰基羟基氨基)戊基]氨基]-1,4-二氧代丁基]羟基氨基]戊基]-N-(5-氨基戊基)-N-羟基琥珀酰胺单盐酸盐
  参考文献：
  名称：

  An efficient total synthesis of desferrioxamine B

  摘要：

  DOI：

  10.1021/jo00249a001
• 作为产物：
  描述：

  O-benzyl-N-(4-cyanobutyl)-hydroxylamine 在 镍 吡啶 、 4-二甲氨基吡啶 、 氨 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 100.0 ℃ 、344.73 kPa 条件下， 反应 40.7h， 生成 6,17,28-tris(benzyloxy)-7,10,18,21,29-pentaoxo-6,11,17,22,28-pentaazatriacontanenitrile
  参考文献：
  名称：

  An efficient total synthesis of desferrioxamine B

  摘要：

  DOI：

  10.1021/jo00249a001
• 作为试剂：
  描述：

  27--6,17-bis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22-tetraazaheptacosanenitrile 、 乙酸酐 在 6,17,28-tris(benzyloxy)-7,10,18,21,29-pentaoxo-6,11,17,22,28-pentaazatriacontanenitrile 、 水 、 氯仿 、 盐酸 、 碳酸氢钠 、 chloroform methanol 作用下， 以 吡啶 为溶剂， 反应 12.0h， 以Column chromatography (5% CH3OH/CHCl3) gave 1.05 g (91%) of (13)的产率得到6,17,28-tris(benzyloxy)-7,10,18,21,29-pentaoxo-6,11,17,22,28-pentaazatriacontanenitrile
  参考文献：
  名称：

  Method for synthesis of desferrioxamine B, analogs and homologs thereof

  摘要：

  使用O-保护，N-保护的羟胺起始合成去铁胺B及其类似物和同系物，其被N-烷基化以产生一个受保护的N-4-氰基烷基羟胺，然后与合适的酸酐酰化。所得的半酸酰胺经过一系列高产率的缩合和还原反应，从而以高总收率得到去铁胺B。或者，通过将活化聚醚与O-保护，N-保护的羟胺反应，并将所得产物经过一系列类似的步骤，可以制备去铁胺B的聚醚类似物。

  公开号：

  US05367113A1

文献信息

• Synthesis and biological evaluation of hydroxamate-based iron chelators
  作者：Raymond J. Bergeron、Jan Wiegand、James S. McManis、P. Thirumalai Perumal

  DOI：10.1021/jm00115a006

  日期：1991.11

  desferrioxamine B (DFO, 1) is described. Hydroxamate reagent 4 was elaborated in a series of high yield steps to the tert-butoxycarbonyl nitrile 11, which provided DFO in three transformations. The intermediate 11 could also be utilized in the preparation of DFO analogues which contain terminal N-acyl groups other than acetyl. The methodology was further employed in the syntheses of the DFO polyether analogues 2

  描述了一种去铁胺X（DFO，1）的新型通用途径。用一系列高产率的步骤将异羟肟酸酯试剂4精制到叔丁氧羰基腈11上，该叔丁氧羰基腈11可通过三个转化提供DFO。中间体11也可以用于制备含有除乙酰基以外的末端N-酰基的DFO类似物。从N-（叔丁氧羰基）-O-苄基羟胺的3,6,9-三氧羰基化开始，该方法进一步用于DFO聚醚类似物2和3的合成中。聚醚2和3是中性分子，比母体DFO亲脂性更高。聚醚异羟肟酸酯2在清除大鼠铁中的功效是去铁胺的近3倍。
• A Versatile Synthesis of Deferrioxamine B
  作者：Raymond J. Bergeron、James S. McManis、Otto IV Phanstiel、J. R. Timothy Vinson

  DOI：10.1021/jo00106a022

  日期：1995.1

  A new and versatile route to N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]-hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide, deferrioxamine B (DFO), is described. The key improvement over the two prior routes was replacement of the nitrile in 2 with a tert-butoxycarbonyl-protected amino terminus. Elimination of the nitrile improved the kinetics of hydrogenation in that the benzyl groups of 12 were cleaved more rapidly than saturation of the cyano group of 2, and a potential overreduction byproduct (4) was thus avoided. N-(Benzyloxy)-1,5-diaminopentane (6) was selectively protected at the primary amino site with a tert-butoxycarbonyl (BOG) group, providing 7. This was reacted at the (benzyloxy)amine with succinic anhydride to produce carboxylic acid 8, which was in turn acylated regiospecifically with diamine 6 at the primary amine to give (benzyloxy)amine 9. The previous two steps were reiterated to afford DFO reagent 11. This synthon allows for modification of DFO at either end of the molecule, thus providing more flexibility in accessing DFO analogues than any prior route. Acetylation of TI, followed by hydrogenolysis and tert-butoxycarbonyl group removal, furnished DFO.
• DIONIS, JOHN B.;JENNY, HANS-BEAT;PETER, HEINRICH H., J. ORG. CHEM., 54,(1989) N3, C. 5623-5627
  作者：DIONIS, JOHN B.、JENNY, HANS-BEAT、PETER, HEINRICH H.

  DOI：——

  日期：——
• BERGERON, RAYMOND J.;PEGRAM, JOSEPH J., J. ORG. CHEM., 53,(1988) N 14, 3131-3134
  作者：BERGERON, RAYMOND J.、PEGRAM, JOSEPH J.

  DOI：——

  日期：——
• Synthesis and analytical characterization of a major desferrioxamine B metabolite
  作者：John B. Dionis、Hans Beat Jenny、Heinrich H. Peter

  DOI：10.1021/jo00284a044

  日期：1989.11