1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-D-erythro-pentofuranosyl]-5-fluorouracil | 529495-97-4

• 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: 1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-D-erythro-pentofuranosyl]-5-fluorouracil
• CAS: 529495-97-4
• 化学式: C₂₉H₃₇FN₂O₄S₃Si
• 分子量: 620.906
• InChiKey: FFEPEVBHOFPMLI-ICDZXHCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  73.58
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-D-erythro-pentofuranosyl]-5-fluorouracil 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以81%的产率得到1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-D-erythro-pentofuranosyl]-5-fluorouracil
  参考文献：
  名称：

  Research on l-Nucleosides. synthesis and biological evaluation of a series of l- and d-2′,3′-Dideoxy-3′-[tris(methylthio)methyl]-β-pentofuranosyl nucleosides

  摘要：

  Novel nucleoside analogues of both D and L enantiomeric series were prepared by coupling reaction between a 2',3'-dideoxy-3'-modified furanose moiety and four different nucleobases. Though in all cases anomeric mixtures of nucleosides were obtained, the presence of the sterically bulky 3-tris(methylthio)methyl group allowed a good stereo selectivity level. All the compounds of both enantiomeric series showed high IC50 values as HSV-1 TK inhibitors and scarce ability to be phosphorylated by HSV-1 TK. In order to overcome possible problems related to the first phosphorylation step and to facilitate the penetration of the molecule through the cellular membrane, a monophosphate prodrug containing a long lipophilic chain was synthesized. No appreciable antiviral activity was exhibited by this molecule. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00460-1
• 作为产物：
  描述：

  (4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one 在 吡啶 、 硫酸氢铵 、 二异丁基氢化铝 、 六甲基二硅氮烷 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.25h， 生成 1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-D-erythro-pentofuranosyl]-5-fluorouracil
  参考文献：
  名称：

  Research on l-Nucleosides. synthesis and biological evaluation of a series of l- and d-2′,3′-Dideoxy-3′-[tris(methylthio)methyl]-β-pentofuranosyl nucleosides

  摘要：

  Novel nucleoside analogues of both D and L enantiomeric series were prepared by coupling reaction between a 2',3'-dideoxy-3'-modified furanose moiety and four different nucleobases. Though in all cases anomeric mixtures of nucleosides were obtained, the presence of the sterically bulky 3-tris(methylthio)methyl group allowed a good stereo selectivity level. All the compounds of both enantiomeric series showed high IC50 values as HSV-1 TK inhibitors and scarce ability to be phosphorylated by HSV-1 TK. In order to overcome possible problems related to the first phosphorylation step and to facilitate the penetration of the molecule through the cellular membrane, a monophosphate prodrug containing a long lipophilic chain was synthesized. No appreciable antiviral activity was exhibited by this molecule. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00460-1