tert-butyl N4-[(benzyloxy)carbonyl]-6-formylcytosine-1-acetate | 1182207-09-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl N4-[(benzyloxy)carbonyl]-6-formylcytosine-1-acetate
• CAS: 1182207-09-5
• 化学式: C₁₉H₂₁N₃O₆
• 分子量: 387.392
• InChiKey: IMIZPDJJANPWAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  116.59
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N4-[(benzyloxy)carbonyl]-6-formylcytosine-1-acetate 、 甲氧羰基亚甲基三苯基正膦 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.83h， 生成 methyl 3-(N4-[(benzyloxy)carbonyl]-1-{[(tert-butoxy)carbonyl]methyl}cytosin-6-yl)propanoate
  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
• 作为产物：
  描述：

  1-(tert-butoxycarbonylmethyl)-4-N-(benzyloxycarbonyl)cytosine 在 正丁基锂 、 二异丙胺 、 N,N-二甲基甲酰胺 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以64%的产率得到tert-butyl N4-[(benzyloxy)carbonyl]-6-formylcytosine-1-acetate
  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