4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol | 259137-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol
• 英文别名: (2R,3S,4R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(6-chloropurin-9-yl)oxolan-3-ol
• CAS: 259137-70-7
• 化学式: C₂₆H₂₉ClN₄O₃Si
• 分子量: 509.08
• InChiKey: PBZBTWWYTRZTJM-XPNTWCBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  82.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol 在 氟化铵 、 氨 作用下， 以 甲醇 为溶剂， 生成 4(R)-(6-amino-9H-purin-9-yl)-2(R)-(hydroxymethyl)tetrahydrofuran-3(S)-ol
  参考文献：
  名称：

  Synthesis and Antiviral Studies of Unsaturated Analogues of Isomeric Dideoxynucleosides

  摘要：

  Novel isomeric dideoxynucleosides with unsaturation in the carbohydrate moiety have been synthesized. For example, isod4A was synthesized through a rearrangement reaction involving a cyclonucleoside. Support for the structures of both purine and pyrimidine d4 compounds came from UV, NMR, HRMS and single crystal Xray data. Interestingly, the single crystal X-ray data for isod4C shows that the base is almost orthogonal to the carbon-carbon double bond of the sugar moiety. Consistent with this is the observation that the UV data of this compound does not show a bathochromic shift compared to the saturated compound implying that the pi-bond is not in conjugation with the pyrimidine base.

  DOI：

  10.1080/07328319908044614
• 作为产物：
  描述：

  2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol 在 palladium on activated charcoal 吡啶 、 盐酸 、 氯化亚砜 、 sodium azide 、 氢气 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~140.0 ℃ 、172.37 kPa 条件下， 反应 19.0h， 生成 4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol
  参考文献：
  名称：

  Synthesis and Antiviral Studies of Unsaturated Analogues of Isomeric Dideoxynucleosides

  摘要：

  Novel isomeric dideoxynucleosides with unsaturation in the carbohydrate moiety have been synthesized. For example, isod4A was synthesized through a rearrangement reaction involving a cyclonucleoside. Support for the structures of both purine and pyrimidine d4 compounds came from UV, NMR, HRMS and single crystal Xray data. Interestingly, the single crystal X-ray data for isod4C shows that the base is almost orthogonal to the carbon-carbon double bond of the sugar moiety. Consistent with this is the observation that the UV data of this compound does not show a bathochromic shift compared to the saturated compound implying that the pi-bond is not in conjugation with the pyrimidine base.

  DOI：

  10.1080/07328319908044614