[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3R)-3-benzamido-3-(furan-2-yl)-2-hydroxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-9-(methylsulfanylmethoxy)-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate | 393547-70-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3R)-3-benzamido-3-(furan-2-yl)-2-hydroxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-9-(methylsulfanylmethoxy)-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 393547-70-1
• 化学式: C₄₇H₅₃NO₁₅S
• 分子量: 904.002
• InChiKey: AFECSJKFNXCTPC-MZXODVADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  64.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  223.43
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3R)-3-benzamido-3-(furan-2-yl)-2-hydroxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-9-(methylsulfanylmethoxy)-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate 在 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以47%的产率得到[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3R)-3-benzamido-3-(furan-2-yl)-2-hydroxypropanoyl]oxy-1-hydroxy-9-(methoxymethoxy)-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Novel C-7 Paclitaxel Ethers:  Discovery of BMS-184476

  摘要：

  The preparation of C-7 paclitaxel ethers is described. Various substituted ethers were prepared via activation of the corresponding methylthiomethyl ether followed by alcohol addition. Variation of the C-7 ether group as well the 3' side chain position led to the discovery of a novel taxane, BMS-184476 (4), with preclinical antitumor activity superior to paclitaxel.

  DOI：

  10.1021/jm0102607
• 作为产物：
  描述：

  7-((甲硫基)甲基)紫杉醇 在 tetrabutylammonium borohydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 16.67h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3R)-3-benzamido-3-(furan-2-yl)-2-hydroxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-9-(methylsulfanylmethoxy)-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Novel C-7 Paclitaxel Ethers:  Discovery of BMS-184476

  摘要：

  The preparation of C-7 paclitaxel ethers is described. Various substituted ethers were prepared via activation of the corresponding methylthiomethyl ether followed by alcohol addition. Variation of the C-7 ether group as well the 3' side chain position led to the discovery of a novel taxane, BMS-184476 (4), with preclinical antitumor activity superior to paclitaxel.

  DOI：

  10.1021/jm0102607