[(1S,5S,6R,7S,10S,11S,13R,16S)-7,13-diacetyloxy-7,11,15,18,18-pentamethyl-3,12-dioxo-10-triethylsilyloxy-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadeca-8,14-dien-16-yl] (2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoate | 670220-85-6

• 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,5S,6R,7S,10S,11S,13R,16S)-7,13-diacetyloxy-7,11,15,18,18-pentamethyl-3,12-dioxo-10-triethylsilyloxy-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadeca-8,14-dien-16-yl] (2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoate
• CAS: 670220-85-6
• 化学式: C₅₃H₇₃NO₁₃Si₂
• 分子量: 988.333
• InChiKey: NYZDTBBMZSUJAY-QMICBCJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  69
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  苯基锂 、 [(1S,5S,6R,7S,10S,11S,13R,16S)-7,13-diacetyloxy-7,11,15,18,18-pentamethyl-3,12-dioxo-10-triethylsilyloxy-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadeca-8,14-dien-16-yl] (2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoate 在 氟化氢吡啶 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 7.0h， 以3%的产率得到Benzoic acid (1S,2S,3R,4S,7S,8S,10R,13S)-4-acetoxy-13-((2R,3S)-3-benzoylamino-2-hydroxy-3-phenyl-propionyloxy)-1,7,10-trihydroxy-4,8,12,15,15-pentamethyl-9-oxo-tricyclo[9.3.1.0^3,8]pentadeca-5,11-dien-2-yl ester
  参考文献：
  名称：

  Synthesis, Modeling, and Anti-Tubulin Activity of a D-Seco Paclitaxel Analogue

  摘要：

  We have previously described a model of paclitaxel-microtubule binding that led to the prediction that analogues of paclitaxel lacking any D ring could stabilize microtubules as well as paclitaxel if the substituent present at C4 did not have unfavorable steric interactions with the binding pocket. We report the synthesis of a 4-methyl paclitaxel analogue, compound 1, which bears this prediction out. Compound 1 is as potent as paclitaxel at microtubule stabilization in vitro; however, it has only about one-four-hundredth the cytotoxicity of paclitaxel.

  DOI：

  10.1021/ol036204c
• 作为产物：
  描述：

  2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-4,20-epoxy-D-seco-paclitaxel 1,2-carbonate 在 platinum(IV) oxide 4-二甲氨基吡啶 、 N,N-二甲基丙烯基脲 、 t-By₄NI 、 氢气 、 sodium cyanoborohydride 、 magnesium bromide 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 81.0h， 生成 [(1S,5S,6R,7S,10S,11S,13R,16S)-7,13-diacetyloxy-7,11,15,18,18-pentamethyl-3,12-dioxo-10-triethylsilyloxy-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadeca-8,14-dien-16-yl] (2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoate
  参考文献：
  名称：

  Synthesis, Modeling, and Anti-Tubulin Activity of a D-Seco Paclitaxel Analogue

  摘要：

  We have previously described a model of paclitaxel-microtubule binding that led to the prediction that analogues of paclitaxel lacking any D ring could stabilize microtubules as well as paclitaxel if the substituent present at C4 did not have unfavorable steric interactions with the binding pocket. We report the synthesis of a 4-methyl paclitaxel analogue, compound 1, which bears this prediction out. Compound 1 is as potent as paclitaxel at microtubule stabilization in vitro; however, it has only about one-four-hundredth the cytotoxicity of paclitaxel.

  DOI：

  10.1021/ol036204c