5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid | 153492-12-7

• 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: 5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid
• 英文别名: 5-Benzyloxy-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid；4-[5-[(2-methylpropan-2-yl)oxycarbonylamino]pentyl-phenylmethoxyamino]-4-oxobutanoic acid
• CAS: 153492-12-7
• 化学式: C₂₁H₃₂N₂O₆
• 分子量: 408.495
• InChiKey: UXIXXBKRQWOLRN-UHFFFAOYSA-N

物化性质

• 密度：
  1.152±0.06 g/cm3(Predicted)
• 溶解度：
  二氯甲烷、乙醚、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid 在 palladium on activated charcoal 吡啶 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0~81.0 ℃ 、101.33 kPa 条件下， 反应 64.33h， 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：

  5-(N-叔丁氧羰基氨基)-1-戊醇 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 2-巯基乙醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.25h， 生成 5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid
  参考文献：
  名称：

  去铁胺 B 全合成的温和模块化方法

  摘要：

  描述了一种温和的模块化方法来全合成世界卫生组织列出的基本药物去铁胺 B。在温和条件下安装异羟肟酸片段，使用通用的不同酰化程序来获得两种单体前体，并使用转移氢化反应来暴露异羟肟酸部分。使用标准酰胺偶联条件，经过十个线性步骤，以甲酸盐形式生成去铁胺 B，总产率为 17%；使用微波辅助酰胺偶联条件，总产率为 13%。

  DOI：

  10.1021/acs.joc.3c02739

文献信息

• [EN] ANTIBACTERIAL SIDEROMYCINS<br/>[FR] SIDÉROMYCINES ANTIBACTÉRIENNES
  申请人：MILLER MARVIN J

  公开号：WO2016027262A1

  公开（公告）日：2016-02-25

  A compound, comprising: an Fe(III)-binding and/or Fe(III)-bound siderophore; one or more optional linker covalently bound to the siderophore; and daptomycin covalently bound to the linker, or, if no linker is present, then to the siderophore; or pharmaceutically acceptable salt or solvate thereof.

  一种化合物，包括：与Fe(III)结合和/或Fe(III)结合的铁载体；一个或多个可选的与铁载体共价结合的连接剂；以及共价结合到连接剂的达托霉素，或者如果没有连接剂存在，则共价结合到铁载体；或其药用可接受的盐或溶剂。
• 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。
• Antibacterial sideromycins
  申请人：Hsiri Therapeutics, Inc.

  公开号：US11149046B2

  公开（公告）日：2021-10-19

  A compound, comprising: an Fe(III)-binding and/or Fe(III)-bound siderophore; one or more optional linker covalently bound to the siderophore; and daptomycin covalently bound to the linker, or, if no linker is present, then to the siderophore; or pharmaceutically acceptable salt or solvate thereof.

  一种化合物，包括：与铁（III）结合和/或与铁（III）结合的苷元；与苷元共价结合的一个或多个任选连接体；与连接体共价结合的达托霉素，或如果不存在连接体，则与苷元共价结合的达托霉素；或其药学上可接受的盐或溶液。
• [EN] REDUCTION-TRIGGERED ANTIBACTERIAL SIDEROMYCINS<br/>[FR] SIDÉROMYCINES ANTIBACTÉRIENNES ACTIVÉES PAR RÉDUCTION
  申请人：MILLER MARVIN J

  公开号：WO2015061630A3

  公开（公告）日：2015-10-29
• Synthesis of novel citrate-based siderophores and siderophore-.beta.-lactam conjugates. Iron transport-mediated drug delivery systems
  作者：Arun Ghosh、Marvin J. Miller

  DOI：10.1021/jo00079a007

  日期：1993.12

  The synthesis of analogs of arthrobactin (5), a microbial iron chelator, and its imide 8 are described. The differentially protected citric acid residue 31 served as the key intermediate in making conjugates having a generalized structure 14 with two representative carbacephalosporin units, 15 and 16. Both conjugates, 49 and 51, showed antibiotic activity, while conjugate 51 obtained from beta-lactam 16 bearing a phenylglycyl side chain was shown to be more effective.