8-[(1-(2-ethoxy-2-oxoethyl)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}hydrazino)methyl]guanine-9-acetic acid | 1182207-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 8-[(1-(2-ethoxy-2-oxoethyl)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}hydrazino)methyl]guanine-9-acetic acid
• 英文别名: 2-[2-amino-8-[[(2-ethoxy-2-oxoethyl)-(9H-fluoren-9-ylmethoxycarbonylamino)amino]methyl]-6-oxo-1H-purin-9-yl]acetic acid
• CAS: 1182207-00-6
• 化学式: C₂₇H₂₇N₇O₇
• 分子量: 561.554
• InChiKey: VXLABMCUZQRIOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  191
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  ethyl 2-(2-{[(9H-fluoren-9-yl)methoxy]carbonyl}hydrazine)acetate 、 tert-butyl 6-O-benzyl-8-(chloromethyl)guanine-9-acetate 在 2,6-二甲基吡啶 、 四丁基溴化铵 、 三乙基硅烷 、 三氟乙酸 作用下， 以 二甲基亚砜 、 二氯甲烷 为溶剂， 以91%的产率得到8-[(1-(2-ethoxy-2-oxoethyl)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}hydrazino)methyl]guanine-9-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).