Benzoic acid (2S,5S)-5-[5-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-[1,3]oxathiolan-2-ylmethyl ester

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: Benzoic acid (2S,5S)-5-[5-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-[1,3]oxathiolan-2-ylmethyl ester
• 英文别名: [(2S,5S)-5-[5-[2-(tert-butoxycarbonylamino)ethylcarbamoyl]-2,4-dioxo-pyrimidin-1-yl]-1,3-oxathiolan-2-yl]methyl benzoate；[(2S,5S)-5-[5-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylcarbamoyl]-2,4-dioxopyrimidin-1-yl]-1,3-oxathiolan-2-yl]methyl benzoate
• 化学式: C₂₃H₂₈N₄O₈S
• 分子量: 520.563
• InChiKey: VJMBUXDEZZDTIX-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  178
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-((S)-2-Benzoyloxymethyl-[1,3]oxathiolan-5-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid 在 N,N'-二异丙基乙二胺 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 Benzoic acid (2S,5S)-5-[5-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-[1,3]oxathiolan-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis and Anti-HIV Evaluation of New 5-Substituted-2′,3′-Dideoxy-3′-thiauridine Nucleosides

  摘要：

  On the basis of molecular modeling calculations using GenMol software, new 5-substituted-2',3'-dideoxy-3'-thiauridine were designed as possible anti-HIV reverse transcriptase inhibitors. The synthesis of the key intermediate 5-carboxy-2',3'-dideoxy-3'-thiauridine was achieved through the condensation of the fully silylated 5-carboxyuracil on 2-benzoyl methyl-5-acetoxy-1,3-oxathiolane using trimethylsilyl triflate (TMSOTf). This latter compound was condensed with 2-(N-tert-Butoxycarbonyl)-1-aminoethane in the presence of N,N-diisopropylethylamine (DIEA). The subsequent carboxamide deprotection led to the final compounds. These new analogues were evaluated for their anti-HIV-1 activities on infected MT(4) cells but no significant protection was observed. Electronic and structural parameters considered in this model were not sufficient to predict any active anti-HIV molecular structures.

  DOI：

  10.1080/07328319608002439