tert-butyl 6-[(1-(2-ethoxy-2-oxoethyl)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}hydrazino)methyl]uracil-1-acetic acid | 1182206-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: tert-butyl 6-[(1-(2-ethoxy-2-oxoethyl)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}hydrazino)methyl]uracil-1-acetic acid
• 英文别名: 2-[6-[[(2-ethoxy-2-oxoethyl)-(9H-fluoren-9-ylmethoxycarbonylamino)amino]methyl]-2,4-dioxopyrimidin-1-yl]acetic acid
• CAS: 1182206-84-3
• 化学式: C₂₆H₂₆N₄O₈
• 分子量: 522.514
• InChiKey: CIUSLHXXVOWDHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  155
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl 6-[(1-(2-ethoxy-2-oxoethyl)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}hydrazino)methyl]uracil-1-acetic acid 在 三乙基硅烷 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 [6-{[1-(2-ethoxy-2-oxoethyl)-2-{[6-({1-(2-ethoxy-2-oxoethyl)-2-[(9H-fluoren-9-ylmethoxy)carbonyl]hydrazinyl}-methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]acetyl}hydrazinyl]methyl}-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]acetic acid
  参考文献：
  名称：

  具有整合的碱基和骨干的寡核苷酸类似物。第28章

  摘要：

  受保护的酰肼联尿嘧啶和腺嘌呤衍生tetranucleoside类似物17,19和21在溶液中，通过偶合二聚体肼合成6和10与羧酸7,11，和16。这些肼和酸被部分地脱保护的肼得到的5,9，和15，将它们通过偶合肼制备3和14与羧酸4和8。完全保护的UU二聚体5的晶体结构分析显示的反平行双链环状与尿嘧啶单元氢键形成经由ħ  N（3）和OC（2）。观察到尿嘧啶单元之间的屈曲度为30.9°，并且尿嘧啶单元II和Fmoc的芴9-基（= 9 H-芴-9-基）甲氧基羰基之间存在堆积相互作用。酰肼ħ  N（3'）和Fmoc的CO基形成分子内氢键。的尿嘧啶和腺嘌呤衍生的，水溶性的酰肼联自身互补八聚体23 - 32和非自互补尿嘧啶衍生十聚体33获得通过偶联羧酸4和8在固体载体上。1个H-NMR分析在CDCl 3，CDCL的混合物3和（d 6）DMSO，和（d 8）THF表明，部分脱保护二聚体5，6，

  DOI：

  10.1002/hlca.201100124
• 作为产物：
  描述：

  tert-butyl 6-[(1-(2-ethoxy-2-oxoethyl)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}hydrazino)methyl]uracil-1-acetate 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到tert-butyl 6-[(1-(2-ethoxy-2-oxoethyl)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}hydrazino)methyl]uracil-1-acetic acid
  参考文献：
  名称：

  具有整合的碱基和骨干的寡核苷酸类似物。第20部分†

  摘要：

  Abstractmagnified imageHydrazide‐ and amide‐linked oligonucleoside analogues with integrated bases and backbone were designed to allow for a rapid synthesis of long and water‐soluble oligomers. The uracil‐, cytosine‐, and adenine‐derived hydrazide building blocks 13–15 were synthesized by nucleophilic substitution with the hydrazine 23 of the halides 19, 28, and 34, derived from the alcohols 18, 27, and 33, respectively, while the uracil‐, cytosine‐, and adenine‐derived amide building blocks 45–47 were synthesized by a Curtius degradation of the carboxylic acids 51, 56, and 61. These acids were obtained by Wittig reaction of the aldehydes 49, 53, and 58. The guanine‐derived monomers 44 and 48 were synthesized by reductive cyclisation of the nitroso amides 38 and 63, respectively, resulting from acylation of the known 2,6‐diamino‐4‐(benzyloxy)‐5‐nitrosopyrimidine (37).

  DOI：

  10.1002/hlca.200900047

文献信息

• Oligonucleotide Analogues with Integrated Bases and Backbone. Part 20
  作者：Manuel Peifer、Fabio De Giacomo、Martin Schandl、Andrea Vasella

  DOI：10.1002/hlca.200900047

  日期：2009.6

  Abstractmagnified imageHydrazide‐ and amide‐linked oligonucleoside analogues with integrated bases and backbone were designed to allow for a rapid synthesis of long and water‐soluble oligomers. The uracil‐, cytosine‐, and adenine‐derived hydrazide building blocks 13–15 were synthesized by nucleophilic substitution with the hydrazine 23 of the halides 19, 28, and 34, derived from the alcohols 18, 27, and 33, respectively, while the uracil‐, cytosine‐, and adenine‐derived amide building blocks 45–47 were synthesized by a Curtius degradation of the carboxylic acids 51, 56, and 61. These acids were obtained by Wittig reaction of the aldehydes 49, 53, and 58. The guanine‐derived monomers 44 and 48 were synthesized by reductive cyclisation of the nitroso amides 38 and 63, respectively, resulting from acylation of the known 2,6‐diamino‐4‐(benzyloxy)‐5‐nitrosopyrimidine (37).
• Oligonucleotide Analogues with Integrated Bases and Backbone. Part 28
  作者：Fabio De Giacomo、Manuel Peifer、Zrinka Rajic、Andrea Vasella

  DOI：10.1002/hlca.201100124

  日期：2011.7

  The protected hydrazide‐linked uracil‐ and adenine‐derived tetranucleoside analogues 17, 19, and 21 were synthesized in solution by coupling the dimeric hydrazines 6 and 10 with the carboxylic acids 7, 11, and 16. These hydrazines and acids were obtained by partially deprotecting the hydrazines 5, 9, and 15, and these were prepared by coupling the hydrazines 3 and 14 with the carboxylic acids 4 and

  受保护的酰肼联尿嘧啶和腺嘌呤衍生tetranucleoside类似物17,19和21在溶液中，通过偶合二聚体肼合成6和10与羧酸7,11，和16。这些肼和酸被部分地脱保护的肼得到的5,9，和15，将它们通过偶合肼制备3和14与羧酸4和8。完全保护的UU二聚体5的晶体结构分析显示的反平行双链环状与尿嘧啶单元氢键形成经由ħ  N（3）和OC（2）。观察到尿嘧啶单元之间的屈曲度为30.9°，并且尿嘧啶单元II和Fmoc的芴9-基（= 9 H-芴-9-基）甲氧基羰基之间存在堆积相互作用。酰肼ħ  N（3'）和Fmoc的CO基形成分子内氢键。的尿嘧啶和腺嘌呤衍生的，水溶性的酰肼联自身互补八聚体23 - 32和非自互补尿嘧啶衍生十聚体33获得通过偶联羧酸4和8在固体载体上。1个H-NMR分析在CDCl 3，CDCL的混合物3和（d 6）DMSO，和（d 8）THF表明，部分脱保护二聚体5，6，