13-[(2'R,3'S)-3'-(N-tert-butoxycarbonyl)amino-2'-triethylsilyloxy-5'-methylhexanoate]-9(R)-dihydro-7,9-isopropylidene-baccatin-III | 345983-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 13-[(2'R,3'S)-3'-(N-tert-butoxycarbonyl)amino-2'-triethylsilyloxy-5'-methylhexanoate]-9(R)-dihydro-7,9-isopropylidene-baccatin-III
• 英文别名: [(1R,2S,5R,7S,11R,12R,15S,17S,18S,19S)-2,12-diacetyloxy-17-hydroxy-9,9,14,19,20,20-hexamethyl-15-[(2R,3S)-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-triethylsilyloxyhexanoyl]oxy-4,8,10-trioxapentacyclo[9.7.1.113,17.02,5.07,19]icos-13-en-18-yl] benzoate
• CAS: 345983-43-9
• 化学式: C₅₂H₇₉NO₁₅Si
• 分子量: 986.282
• InChiKey: DMNRITWDCPSYRF-IGQAXPDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.12
• 重原子数：
  69
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  201
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  13-[(2'R,3'S)-3'-(N-tert-butoxycarbonyl)amino-2'-triethylsilyloxy-5'-methylhexanoate]-9(R)-dihydro-7,9-isopropylidene-baccatin-III 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 13.0h， 以90%的产率得到13-[(2'R,3'S)-3'-(N-tert-butoxycarbonyl)amino-2'-hydroxy-5'-methylhexanoate]-9(R)-dihydro-baccatin-III
  参考文献：
  名称：

  An Efficient Synthesis of the Taxane-Derived Anticancer Agent ABT-271

  摘要：

  ABT-271, 1, has been identified as a promising anticancer agent. ABT-271 is a novel taxane possessing a CS-(R)-hydroxyl group as opposed to a CS-ketone which is present in Taxol and Taxotere. To further evaluate ABT-271 as a potential anticancer agent, an efficient synthesis was developed which allows the large scale synthesis of ABT-271. Ketalization of the 7,9-diol of 9-DHAB-III, 2, allows selective removal of th:e CI-acetate with phenyllithium. The resulting C13-hydroxyl group is then acylated using LiHMDS and beta -lactam 22 to give ABT-271 in protected form. The protecting groups were removed first by acidic hydrolysis followed by basic hydrolysis to provide ABT-271. Application of this synthetic sequence provided over 600 g of ABT-271, 1.

  DOI：

  10.1021/jo0057203
• 作为产物：
  描述：

  iso-propyl (2R,3S)-3-amino-2-hydroxy-5-methylhexanoate 在 4-二甲氨基吡啶 、 potassium fluoride 、 叔丁基氯化镁 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 9.5h， 生成 13-[(2'R,3'S)-3'-(N-tert-butoxycarbonyl)amino-2'-triethylsilyloxy-5'-methylhexanoate]-9(R)-dihydro-7,9-isopropylidene-baccatin-III
  参考文献：
  名称：

  An Efficient Synthesis of the Taxane-Derived Anticancer Agent ABT-271

  摘要：

  ABT-271, 1, has been identified as a promising anticancer agent. ABT-271 is a novel taxane possessing a CS-(R)-hydroxyl group as opposed to a CS-ketone which is present in Taxol and Taxotere. To further evaluate ABT-271 as a potential anticancer agent, an efficient synthesis was developed which allows the large scale synthesis of ABT-271. Ketalization of the 7,9-diol of 9-DHAB-III, 2, allows selective removal of th:e CI-acetate with phenyllithium. The resulting C13-hydroxyl group is then acylated using LiHMDS and beta -lactam 22 to give ABT-271 in protected form. The protecting groups were removed first by acidic hydrolysis followed by basic hydrolysis to provide ABT-271. Application of this synthetic sequence provided over 600 g of ABT-271, 1.

  DOI：

  10.1021/jo0057203