N4-p-bromobenzoyl-2',3'-O-isopropylidene-O2,5'-cyclocytidine | 1386977-60-1

• 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: N4-p-bromobenzoyl-2',3'-O-isopropylidene-O2,5'-cyclocytidine
• 英文别名: 4-bromo-N-[(1R,10R,11R,15R)-13,13-dimethyl-8,12,14,16-tetraoxa-2,6-diazatetracyclo[8.5.1.02,7.011,15]hexadeca-3,6-dien-5-ylidene]benzamide
• CAS: 1386977-60-1
• 化学式: C₁₉H₁₈BrN₃O₅
• 分子量: 448.273
• InChiKey: HPGAMEXOMGTIHJ-DNNBLBMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  82
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N4-p-bromobenzoyl-2',3'-O-isopropylidene-O2,5'-cyclocytidine 在 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.5h， 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
• 作为产物：
  描述：

  胞苷 在 吡啶 、 三甲基氯硅烷 、 高氯酸 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 9.25h， 生成 N4-p-bromobenzoyl-2',3'-O-isopropylidene-O2,5'-cyclocytidine
  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.