(1R,2S,3S,5R)-2-[(2-amino-6-chloro-5-(4-chlorophenyldiazenyl)pyrimidin-4-ylamino)methyl]-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol | 1239953-44-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,3S,5R)-2-[(2-amino-6-chloro-5-(4-chlorophenyldiazenyl)pyrimidin-4-ylamino)methyl]-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol
• CAS: 1239953-44-6
• 化学式: C₂₀H₂₄Cl₂N₆O₂
• 分子量: 451.356
• InChiKey: APWWTCQRHBEJRU-XICGMEGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129.01
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,5R)-2-[(2-amino-6-chloro-5-(4-chlorophenyldiazenyl)pyrimidin-4-ylamino)methyl]-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol 在 溶剂黄146 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以73%的产率得到(1R,2S,3S,5R)-2-[(2,5-diamino-6-chloropyrimidin-4-ylamino)methyl]-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol
  参考文献：
  名称：

  Carbocyclic nucleosides from enantiomeric, α-pinane-based aminodiols

  摘要：

  Starting from (1R,25,3S.5R)- and (15,2R,3R,5S)-6,6-dimethylspiro[bicyclo[3 1.1]heptane-2.2'-oxiran]-3-ol (-)-8 and (+)-8, two comparative syntheses were developed for pinane-based chiral carbocyclic nucleosides The regioselective ring opening of the spiro-oxirane ring of (-)-8 and (+)-8 with NaN(3) resulted in azidodiols (-)-9 and (+)-9. Catalytic reduction of (-)-9 and (+)-9 furnished chiral aminodiols (-)-10 and (+)-10, which were transformed by linear synthesis to purine-type nucleosides 16-18 through pyrimidine intermediates. Regioselective ring opening of the oxirane ring of ( -)-8 and (+)-8 resulted in adenine-. cytosine- and uracil-based carbocyclic nucleosides 19-21 in a single-step synthesis (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.04.054
• 作为产物：
  描述：

  (1R,2S,3S,5R)-2-[(2-amino-6-chloropyrimidin-4-ylamino)methyl]-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol 、 对氯苯胺 在 盐酸 、 sodium nitrite 、 sodium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 以91%的产率得到(1R,2S,3S,5R)-2-[(2-amino-6-chloro-5-(4-chlorophenyldiazenyl)pyrimidin-4-ylamino)methyl]-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol
  参考文献：
  名称：

  Carbocyclic nucleosides from enantiomeric, α-pinane-based aminodiols

  摘要：

  Starting from (1R,25,3S.5R)- and (15,2R,3R,5S)-6,6-dimethylspiro[bicyclo[3 1.1]heptane-2.2'-oxiran]-3-ol (-)-8 and (+)-8, two comparative syntheses were developed for pinane-based chiral carbocyclic nucleosides The regioselective ring opening of the spiro-oxirane ring of (-)-8 and (+)-8 with NaN(3) resulted in azidodiols (-)-9 and (+)-9. Catalytic reduction of (-)-9 and (+)-9 furnished chiral aminodiols (-)-10 and (+)-10, which were transformed by linear synthesis to purine-type nucleosides 16-18 through pyrimidine intermediates. Regioselective ring opening of the oxirane ring of ( -)-8 and (+)-8 resulted in adenine-. cytosine- and uracil-based carbocyclic nucleosides 19-21 in a single-step synthesis (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.04.054