2'-O-(t-butyldimethylsilyl)-7-deoxy-7β-thiopaclitaxel | 215246-66-5

• 英文名称: 2'-O-(t-butyldimethylsilyl)-7-deoxy-7β-thiopaclitaxel
• 英文别名: [(1S,2S,3R,4S,7R,9S,10R,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-sulfanyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 215246-66-5
• 化学式: C₅₃H₆₅NO₁₃SSi
• 分子量: 984.25
• InChiKey: ITZMBRKPOKIXCJ-CIOAKVLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  69
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  191
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2'-O-(t-butyldimethylsilyl)-7-deoxy-7β-thiopaclitaxel 在 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.16h， 生成 7-deoxy-7β-methylthiopaclitaxel
  参考文献：
  名称：

  Synthesis of 7β-Sulfur Analogues of Paclitaxel Utilizing a Novel Epimerization of the 7α-Thiol Group

  摘要：

  [GRAPHICS]90 degreesCPaclitaxel analogues with a sulfur group at the 7 beta position were required for SAR studies, Attempts to generate these compounds by displacing a 7 alpha leaving group with sulfur nucleophiles were unsuccessful. Instead, these compounds were successfully prepared from a 7 beta -thiol intermediate that was obtained by a base-catalyzed epimerization of the 7 alpha -thiol derivative. The epimerization presumably proceeds through a thioaldehyde intermediate and exhibits the opposite stereochemical preference of its oxygen counterpart.

  DOI：

  10.1021/ol015727m
• 作为产物：
  描述：

  2'-O-(叔-丁基二甲基硅烷基)紫杉醇7-O-三氟甲烷磺酸酯 在 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 64.5h， 生成 2'-O-(t-butyldimethylsilyl)-7-deoxy-7β-thiopaclitaxel
  参考文献：
  名称：

  Synthesis of 7β-Sulfur Analogues of Paclitaxel Utilizing a Novel Epimerization of the 7α-Thiol Group

  摘要：

  [GRAPHICS]90 degreesCPaclitaxel analogues with a sulfur group at the 7 beta position were required for SAR studies, Attempts to generate these compounds by displacing a 7 alpha leaving group with sulfur nucleophiles were unsuccessful. Instead, these compounds were successfully prepared from a 7 beta -thiol intermediate that was obtained by a base-catalyzed epimerization of the 7 alpha -thiol derivative. The epimerization presumably proceeds through a thioaldehyde intermediate and exhibits the opposite stereochemical preference of its oxygen counterpart.

  DOI：

  10.1021/ol015727m