1-(tert-Butoxycarbonyl)-7,18,29-trihydroxy-8,11,19,22,30-pentaoxo-1,7,12,18,23,29-hexaazahentriacontane | 106339-54-2

• 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-trihydroxy-8,11,19,22,30-pentaoxo-1,7,12,18,23,29-hexaazahentriacontane
• 英文别名: tert-butyl N-[5-[[4-[5-[[4-[5-[acetyl(hydroxy)amino]pentylamino]-4-oxobutanoyl]-hydroxyamino]pentylamino]-4-oxobutanoyl]-hydroxyamino]pentyl]carbamate
• CAS: 106339-54-2
• 化学式: C₃₀H₅₆N₆O₁₀
• 分子量: 660.809
• InChiKey: BRHGXKBAMCTQEM-UHFFFAOYSA-N

物化性质

• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  46
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  218
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(tert-Butoxycarbonyl)-7,18,29-trihydroxy-8,11,19,22,30-pentaoxo-1,7,12,18,23,29-hexaazahentriacontane 、 三氟乙酸 反应 0.33h， 生成 Deferrioxamine B trifluoroacetate
  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：

  1-(tert-Butoxycarbonyl)-7,18,29-tris(benzyloxy)-8,11,19,22,30-pentaoxo-1,7,12,18,23,29-hexaazahentriacontane 在 钯 氮气 、 氢气 、 ( 10-15μ ) 、 甲醇 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、13.51 MPa 条件下， 反应 0.33h， 以to provide 199 mg (81%) of (13) as an amorphous white solid的产率得到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：

  Method for preparing desferrioxamine B and homologs thereof

  摘要：

  本文介绍了一种新颖且多用途的制备去铁胺B（DFO）的方法，即将N-苄氧基-1,5-二氨基戊烷选择性地保护在主要氨基位点，然后在苄氧胺上与酸酐反应生成羧酸，再与二胺在主要胺基上区域特异性地酰化得到苄氧基胺。以上两个步骤重复进行，得到DFO试剂。对DFO试剂进行乙酰化，然后进行氢解和叔丁氧羰基基团去除，即可得到DFO。

  公开号：

  US05493053A1

文献信息

• Synthesis and characterization of a triazine dendrimer that sequesters iron(III) using 12 desferrioxamine B groups
  作者：Jongdoo Lim、Vincent J. Venditto、Eric E. Simanek

  DOI：10.1016/j.bmc.2010.05.039

  日期：2010.8

  The synthesis of a third generation triazine dendrimer, 1, containing multiple, iron-sequestering desferrioxamine B (DFO) groups is described. Benzoylation of the hydroxamic acid groups of DFO and formation of a reactive dichlorotriazine provide the intermediate for reaction with the second generation dendrimer displaying twelve amines. This strategy further generalizes the ‘functional monomer’ approach

  描述了包含多个铁螯合去铁胺 B (DFO) 基团的第三代三嗪树枝状聚合物1的合成。DFO 的异羟肟酸基团的苯甲酰化和反应性二氯三嗪的形成提供了与显示十二个胺的第二代树枝状聚合物反应的中间体。该策略进一步推广了“功能单体”方法，以生成具有生物活性的三嗪树枝状聚合物。树枝状聚合物1分七个步骤制备，总产率为 35%，显示 12 个 DFO 基团，使其药物重量为 56%。分光光度法滴定 (UV-vis) 表明1螯合铁（III）原子，既没有协同性，也没有来自树枝状聚合物骨架的显着干扰。从NMR谱和质谱测定证据表明限制于该官能化单体的方法：痕量ø -到- ñ酰基转移从受保护的异羟肟酸与胺封端的树枝状聚合物的偶联步骤导致显示更少的N-苯甲酰化的树枝状聚合物过程中发生超过 12 个 DFO 组。
• [EN] POLYAMINE-METAL CHELATOR CONJUGATES<br/>[FR] CONJUGUES POLYAMINE-CHELATEUR DE METAL
  申请人：UNIV FLORIDA

  公开号：WO2005023310A3

  公开（公告）日：2005-04-21
• 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.