[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 3-azidobenzoate | 156266-05-6

• 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,3S)-3-benzamido-3-phenyl-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 3-azidobenzoate
• CAS: 156266-05-6
• 化学式: C₅₉H₇₈N₄O₁₄Si₂
• 分子量: 1123.46
• InChiKey: IOXMXNUFHIBJML-SDXTULIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.74
• 重原子数：
  79.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  248.05
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 3-azidobenzoate 在 吡啶 、 盐酸 、 甲醇 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.92h， 生成
  参考文献：
  名称：

  Synthesis and biological activity of A-nor-paclitaxel analogues

  摘要：

  A number of paclitaxel analogues with a 5-membered A-ring (A-nor-paclitaxels, or (15 right-arrow 1)-abeo-paclitaxels) have been prepared in order to determine whether analogues of this class might have improved bioactivity as compared with paclitaxel. Most of the compounds synthesized were less active than paclitaxel, but one analogue was equivalent to paclitaxel in a tubulin-assembly assay, and another analogue was more cytotoxic than paclitaxel in two different cell lines of the NCI screen.

  DOI：

  10.1016/s0968-0896(97)00035-7
• 作为产物：
  描述：

  (2'R,3'S)-2',7-(bis)triethylsilyl taxol 在 sodium hydroxide 、 四丁基硫酸氢铵 、 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.08h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 3-azidobenzoate
  参考文献：
  名称：

  Synthesis and biological activity of A-nor-paclitaxel analogues

  摘要：

  A number of paclitaxel analogues with a 5-membered A-ring (A-nor-paclitaxels, or (15 right-arrow 1)-abeo-paclitaxels) have been prepared in order to determine whether analogues of this class might have improved bioactivity as compared with paclitaxel. Most of the compounds synthesized were less active than paclitaxel, but one analogue was equivalent to paclitaxel in a tubulin-assembly assay, and another analogue was more cytotoxic than paclitaxel in two different cell lines of the NCI screen.

  DOI：

  10.1016/s0968-0896(97)00035-7

文献信息

• Unexpectedly Facile Hydrolysis of the 2-Benzoate Group of Taxol and Syntheses of Analogs with Increased Activities
  作者：Ashok G. Chaudhary、Milind M. Gharpure、John M. Rimoldi、Mahendra D. Chordia、David G. I. Kingston、Surinder Grover、Chii M. Lin、Ernest Hamel、A. A. Leslie Gunatilaka

  DOI：10.1021/ja00088a063

  日期：1994.5