lysidine trifluoroacetate | 1386977-73-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: lysidine trifluoroacetate
• 英文别名: (2S)-2-amino-6-[[4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-ylidene]amino]hexanoic acid;2,2,2-trifluoroacetic acid
• CAS: 1386977-73-6
• 化学式: C₂HF₃O₂*C₁₅H₂₅N₅O₆
• 分子量: 485.417
• InChiKey: ZRMVSZUJRVBKSM-ZGVNSRHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.81
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  225
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  N4-p-bromobenzoyl-2',3'-isopropylidenecytidine 在 偶氮二甲酸二异丙酯 、 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 11.5h， 生成 lysidine trifluoroacetate
  参考文献：
  名称：

  Efficient Preparation of 2,4-Diaminopyrimidine Nucleosides: Total Synthesis of Lysidine and Agmatidine

  摘要：

  An efficient route for the synthesis of 2,4-diaminopyrimidine ribosides from cytidine is described consisting of six steps with overall yields >50% and only one chromatographic step. The key amine addition step utilizes LiCl and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to ensure clean conversion to a single tautomeric product. This route has been used to prepare the modified tRNA nucleosides lysidine and agmatidine in quantities suitable for structural characterization.

  DOI：

  10.1021/ol301769j

文献信息

• Efficient Preparation of 2,4-Diaminopyrimidine Nucleosides: Total Synthesis of Lysidine and Agmatidine
  作者：Brett J. Kopina、Charles T. Lauhon

  DOI：10.1021/ol301769j

  日期：2012.8.17

  An efficient route for the synthesis of 2,4-diaminopyrimidine ribosides from cytidine is described consisting of six steps with overall yields >50% and only one chromatographic step. The key amine addition step utilizes LiCl and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to ensure clean conversion to a single tautomeric product. This route has been used to prepare the modified tRNA nucleosides lysidine and agmatidine in quantities suitable for structural characterization.