1-(tert-Butoxycarbonyl)-7,18,29-tris(benzyloxy)-8,11,19,22-tetraoxo-1,7,12,18,23,29-hexaazanonacosane | 160388-24-9

• 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: 1-(tert-Butoxycarbonyl)-7,18,29-tris(benzyloxy)-8,11,19,22-tetraoxo-1,7,12,18,23,29-hexaazanonacosane
• 英文别名: tert-butyl N-[5-[[4-oxo-4-[5-[[4-oxo-4-[5-(phenylmethoxyamino)pentylamino]butanoyl]-phenylmethoxyamino]pentylamino]butanoyl]-phenylmethoxyamino]pentyl]carbamate
• CAS: 160388-24-9
• 化学式: C₄₉H₇₂N₆O₉
• 分子量: 889.145
• InChiKey: NNXOMMZCUGSLCB-UHFFFAOYSA-N

物化性质

• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  64
• 可旋转键数：
  35
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  177
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(tert-Butoxycarbonyl)-7,18,29-tris(benzyloxy)-8,11,19,22-tetraoxo-1,7,12,18,23,29-hexaazanonacosane 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 24.33h， 生成 1-(tert-Butoxycarbonyl)-7,18,29-trihydroxy-8,11,19,22,30-pentaoxo-1,7,12,18,23,29-hexaazahentriacontane
  参考文献：
  名称：

  A Versatile Synthesis of Deferrioxamine B

  摘要：

  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.

  DOI：

  10.1021/jo00106a022
• 作为产物：
  描述：

  tert-butyl [5-[(Benzyloxy)amino]pentyl]carbamate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 41.5h， 生成 1-(tert-Butoxycarbonyl)-7,18,29-tris(benzyloxy)-8,11,19,22-tetraoxo-1,7,12,18,23,29-hexaazanonacosane
  参考文献：
  名称：

  A Versatile Synthesis of Deferrioxamine B

  摘要：

  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.

  DOI：

  10.1021/jo00106a022

文献信息

• Method for preparing desferrioxamine B and homologs thereof
  申请人：University of Florida Research Foundation, Inc.

  公开号：US05493053A1

  公开（公告）日：1996-02-20

  A new and versatile route to N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamin o]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide, desferrioxamine B (DFO) is described. N-Benzyloxy-1,5-diaminopentane is selectively protected at the primary amino site. The product is reacted at the benzyloxyamine with an anhydride to produce a carboxylic acid which is, in turn, acylated regio-specifically with a diamine at the primary amine to give a benzyloxyamine. The previous two steps are repeated to afford a DFO reagent. Acetylation of the DFO reagent, followed by hydrogenolysis and tert-butoxycarbonyl group removal, furnishes DFO.

  本文介绍了一种新的多功能途径，用于制备N'-[5-[[4-[[5-(乙酰羟胺基)戊基]氨基]-1,4-二氧戊基]羟胺基]戊基]-N-(5-氨基戊基)-N-羟基丁二酰胺，即去铁胺B（DFO）。选择性保护N-苯甲氧基-1,5-二氨基戊烷的主要氨基官能团，然后在苯甲氧胺基处与酸酐反应，产生一个羧酸，再以另一种二胺在主要胺基位置上进行区域特异性的酰化，从而得到一个苯甲氧胺基。重复前两个步骤，以制备DFO试剂。对DFO试剂进行乙酰化处理，随后进行氢解和叔丁氧羰基基团去除，即可得到DFO。
• METHOD FOR PREPARING DESFERRIOXAMINE B AND HOMOLOGS THEREOF
  申请人：UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.

  公开号：EP0799192A1

  公开（公告）日：1997-10-08
• US5493053A
  申请人：——

  公开号：US5493053A

  公开（公告）日：1996-02-20
• 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.