1-[2',3'-di-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine-5'-bis(S-pivaloyl-2-thioethyl)phosphate | 913959-47-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 1-[2',3'-di-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine-5'-bis(S-pivaloyl-2-thioethyl)phosphate
• CAS: 913959-47-4
• 化学式: C₃₅H₆₆N₃O₁₀PS₂Si₂
• 分子量: 840.2
• InChiKey: LJRBMHWHOCNNOI-AOGFTHLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.27
• 重原子数：
  53.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  167.5
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  1-[2',3'-di-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine-5'-bis(S-pivaloyl-2-thioethyl)phosphate 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 生成 ((2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl bis(S-pivaloyl-2-mercaptoethan-1-yl)phosphate
  参考文献：
  名称：

  Prodrugs of Ara-CMP and Ara-AMP with aS-Acyl-2-thioethyl (SATE) Biolabile Phosphate Protecting Group: Synthesis and Biological Evaluation

  摘要：

  The bis(S-pivaloyl-2-thioethyl) phosphotriesters of Ara-C and Ara-A were synthesized as potential bioreversible mononucleotide prodrugs. Some N- and O-acylated derivatives were also prepared with the aim to modify the lipophilicity of the title pronucleotides. Compounds were tested far their antitumor/antiviral activity against a variety of tumor cells and viruses.

  DOI：

  10.1080/15257779908041616
• 作为产物：
  描述：

  阿糖胞苷 在 咪唑 、 四氮唑 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 溶剂黄146 作用下， 以 癸烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.0h， 生成 1-[2',3'-di-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine-5'-bis(S-pivaloyl-2-thioethyl)phosphate
  参考文献：
  名称：

  Synthetic Approaches to a Mononucleotide Prodrug of Cytarabine

  摘要：

  Synthetic pathways to a mononucleotide prodrug of cytarabine (Ara-C) bearing S-pivaloyl-2-thioethyl (tBuSATE) groups, as biolabile phosphate protections, are reported. Using a common phosphoramidite approach, two different kinds of nucleoside protecting groups have been investigated. During this study, we observed an intermolecular migration of the Boc protecting group in the course of the tert-butyldimethylsilyl ether cleavage using tetrabutyl ammonium fluoride.

  DOI：

  10.1080/15257770500267006