bis-O-(tert-butyldiphenylsilyl)-4-(1-acetoxyvinyl)-6-methylsalicyl alcohol | 1095170-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: bis-O-(tert-butyldiphenylsilyl)-4-(1-acetoxyvinyl)-6-methylsalicyl alcohol
• 英文别名: 1-[4-[Tert-butyl(diphenyl)silyl]oxy-3-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-methylphenyl]ethenyl acetate
• CAS: 1095170-85-6
• 化学式: C₄₄H₅₀O₄Si₂
• 分子量: 699.05
• InChiKey: HDXDICPUSIQPPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.54
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis-O-(tert-butyldiphenylsilyl)-4-(1-acetoxyvinyl)-6-methylsalicyl alcohol 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以82%的产率得到4-(1-acetoxyvinyl)-6-methylsalicyl alcohol
  参考文献：
  名称：

  5-(1-Acetoxyvinyl)-cycloSaligenyl-2′,3′-dideoxy-2′,3′- didehydrothymidine Monophosphates, a Second Type of New, Enzymatically Activated cycloSaligenyl Pronucleotides

  摘要：

  In our attempt to further develop the cycloSal pronucleotide concept, we report oil 5-(1-acetoxyvinyl)-cycloSal-d4TMPs as a new type of enzyme-activated pronucleotides. These compounds were converted into 5-acetyl-cycloSal-d4TMPs by (carboxy)esterase cleavage inside the cells. The enzymatic reaction led to the formation of a strong electron-withdrawing substituent that strongly accelerates the chemical hydrolysis of the cycloSal nucleotide to give d4TMP. For some cycloSal-d4TMPs a separation into the diastereomers was achieved. The absolute configuration was assigned by correlation of circular dichroism spectra with similar compounds. Most of the compounds showed complete retention of antiviral activity in TK-deficient CEM/TK- cells, which proves the TK-bypass potential of this approach. Interestingly, (S-p)-isomers of cycloSal phosphate triesters showed better antiviral activity in HIV-2-infected thymidine-kinase deficient CEM/TK- cells than their (R-p)-counterparts.

  DOI：

  10.1021/jm801197f
• 作为产物：
  描述：

  乙酸异丙烯酯 、 bis-O-(tert-butyldiphenylsilyl)-4-acetyl-6-methylsalicyl alcohol 在 对甲苯磺酸 作用下， 反应 18.0h， 以69%的产率得到bis-O-(tert-butyldiphenylsilyl)-4-(1-acetoxyvinyl)-6-methylsalicyl alcohol
  参考文献：
  名称：

  5-(1-Acetoxyvinyl)-cycloSaligenyl-2′,3′-dideoxy-2′,3′- didehydrothymidine Monophosphates, a Second Type of New, Enzymatically Activated cycloSaligenyl Pronucleotides

  摘要：

  In our attempt to further develop the cycloSal pronucleotide concept, we report oil 5-(1-acetoxyvinyl)-cycloSal-d4TMPs as a new type of enzyme-activated pronucleotides. These compounds were converted into 5-acetyl-cycloSal-d4TMPs by (carboxy)esterase cleavage inside the cells. The enzymatic reaction led to the formation of a strong electron-withdrawing substituent that strongly accelerates the chemical hydrolysis of the cycloSal nucleotide to give d4TMP. For some cycloSal-d4TMPs a separation into the diastereomers was achieved. The absolute configuration was assigned by correlation of circular dichroism spectra with similar compounds. Most of the compounds showed complete retention of antiviral activity in TK-deficient CEM/TK- cells, which proves the TK-bypass potential of this approach. Interestingly, (S-p)-isomers of cycloSal phosphate triesters showed better antiviral activity in HIV-2-infected thymidine-kinase deficient CEM/TK- cells than their (R-p)-counterparts.

  DOI：

  10.1021/jm801197f