[(1S,2S,3R,4S,7R,9S,10S,12R)-4-acetyloxy-1,12-dihydroxy-10,14,17,17-tetramethyl-11,15-dioxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 4-(dimethylamino)benzoate | 163351-90-4

• 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)-4-acetyloxy-1,12-dihydroxy-10,14,17,17-tetramethyl-11,15-dioxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 4-(dimethylamino)benzoate
• CAS: 163351-90-4
• 化学式: C₃₇H₅₃NO₁₀Si
• 分子量: 699.914
• InChiKey: DFIRFIGAECNVFI-OZARNXOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  49.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  148.9
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  [(1S,2S,3R,4S,7R,9S,10S,12R)-4-acetyloxy-1,12-dihydroxy-10,14,17,17-tetramethyl-11,15-dioxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 4-(dimethylamino)benzoate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium hexamethyldisilazane 、 氟化氢吡啶 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 4-(dimethylamino)benzoate
  参考文献：
  名称：

  Nicolaou, Kyriacos Costa; Couladouros, E. A.; Nantermet, P. G., Angewandte Chemie, 1994, vol. 106, # 15/16, p. 1669 - 1671

  摘要：

  DOI：
• 作为产物：
  描述：

  [4-(二甲基氨基)苯基]锂 、 [(1S,5S,6R,7S,10R,12S,13S,15R)-15-hydroxy-13,17,20,20-tetramethyl-3,14,18-trioxo-12-triethylsilyloxy-2,4,9-trioxapentacyclo[14.3.1.01,5.06,13.07,10]icos-16-en-7-yl] acetate 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， 反应 0.25h， 以30%的产率得到[(1S,2S,3R,4S,7R,9S,10S,12R)-4-acetyloxy-1,12-dihydroxy-10,14,17,17-tetramethyl-11,15-dioxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 4-(dimethylamino)benzoate
  参考文献：
  名称：

  Chemical Synthesis and Biological Evaluation of C-2 Taxoids

  摘要：

  An efficient, general method for the synthesis of 1,2-hydroxy esters by regioselective nucleophilic opening of 1,2-cyclic carbonate systems has been developed. A reliable and practical route giving access to the taxoid carbonate 2 from the readily available 10-deacetylbaccatin III (13) has been established. Nucleophilic opening of the carbonate 2 with a variety of nucleophiles provided a number of novel C-2 Taxols. Water-soluble taxoid onium salts (e.g., 31e, 31n, 32, and 34b) were also synthesized and studied. A selected number of taxoids were subjected to cytotoxicity and tubulin polymerization assays as well as in vivo studies. The results of these studies are reported herein.

  DOI：

  10.1021/ja00114a005