氯法拉滨杂质12 | 1140251-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 氯法拉滨杂质12
• 中文别名: 克罗拉滨杂质9
• 英文名称: (2R,3R,4S,5R)-5-(6-amino-2-chloro-5-formamidopyrimidin-4-ylamino)-2-(benzoyloxymethyl)-4-fluorotetrahydrofuran-3-yl benzoate
• 英文别名: (2R,3R,4S,5R)-5-((6-Amino-2-chloro-5-formamidopyrimidin-4-yl)amino)-2-((benzoyloxy)methyl)-4-fluorotetrahydrofuran-3-yl benzoate；[(2R,3R,4S,5R)-5-[(6-amino-2-chloro-5-formamidopyrimidin-4-yl)amino]-3-benzoyloxy-4-fluorooxolan-2-yl]methyl benzoate
• CAS: 1140251-41-7
• 化学式: C₂₄H₂₁ClFN₅O₆
• 分子量: 529.912
• InChiKey: DLNGRMRXAPWPTA-VWFIUDSGSA-N

物化性质

• 熔点：
  203-205 °C
• 沸点：
  804.2±65.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于乙腈、氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  154.76
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  氯法拉滨杂质12 在 甲醇 、 sodium methylate 作用下， 反应 20.5h， 以52%的产率得到克罗拉滨杂质7
  参考文献：
  名称：

  Synthetic Studies on Formamidopyrimidines Related to Clofarabine

  摘要：

  Degradation of clofarabine (3) in 0.9% saline solution at 100C afforded three degradation products which were determined to be formamidopyrimidines 4-6.Compounds 4 and 5 were assigned as C(1)' anomers on the basis of one-dimensional and two-dimensional NMR experiments, whereas 6 was found to be the formamidopyrimidine lacking the sugar moiety. An improved procedure for the synthesis of formamidopyrimidines was developed, wherein benzoylated clofarabine (11) was treated with allyl chloroformate, followed by deprotection of the alloc group with catalytic Pd(PPh(3))(4) and dimedone. A synthesis of compound 6 from 4 is also described.

  DOI：

  10.1080/15257770802257770
• 作为产物：
  描述：

  (2R,3R,4S,5R)-5-(5-(N-(allyloxycarbonyl)formamido)-6-amino-2-chloropyrimidin-4-ylamino)-2-(benzoyloxymethyl)-4-fluorotetrahydrofuran-3-yl benzoate 在 四(三苯基膦)钯 5,5-二甲基-1,3-环己二酮 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以30%的产率得到氯法拉滨杂质12
  参考文献：
  名称：

  Synthetic Studies on Formamidopyrimidines Related to Clofarabine

  摘要：

  Degradation of clofarabine (3) in 0.9% saline solution at 100C afforded three degradation products which were determined to be formamidopyrimidines 4-6.Compounds 4 and 5 were assigned as C(1)' anomers on the basis of one-dimensional and two-dimensional NMR experiments, whereas 6 was found to be the formamidopyrimidine lacking the sugar moiety. An improved procedure for the synthesis of formamidopyrimidines was developed, wherein benzoylated clofarabine (11) was treated with allyl chloroformate, followed by deprotection of the alloc group with catalytic Pd(PPh(3))(4) and dimedone. A synthesis of compound 6 from 4 is also described.

  DOI：

  10.1080/15257770802257770