4-O-[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,15-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-12-yl] 1-O-[(1R,3R,5S,7S,8S,9R,10R,13S)-7,9,10-triacetyloxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-tricyclo[9.3.1.03,8]pentadec-11-enyl] butanedioate | 237428-99-8

• 英文名称: 4-O-[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,15-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-12-yl] 1-O-[(1R,3R,5S,7S,8S,9R,10R,13S)-7,9,10-triacetyloxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-tricyclo[9.3.1.03,8]pentadec-11-enyl] butanedioate
• CAS: 237428-99-8
• 化学式: C₇₁H₁₀₄O₂₀Si₂
• 分子量: 1333.77
• InChiKey: BGYRLEBCEHTMKY-JTBJRRHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.89
• 重原子数：
  93.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  269.32
• 氢给体数：
  2.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  肉桂酸 、 4-O-[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,15-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-12-yl] 1-O-[(1R,3R,5S,7S,8S,9R,10R,13S)-7,9,10-triacetyloxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-tricyclo[9.3.1.03,8]pentadec-11-enyl] butanedioate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以70%的产率得到4-O-[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,15-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-12-yl] 1-O-[(1R,3R,5S,7S,8S,9R,10R,13S)-7,9,10-triacetyloxy-8,12,15,15-tetramethyl-4-methylidene-5-[(E)-3-phenylprop-2-enoyl]oxy-13-tricyclo[9.3.1.03,8]pentadec-11-enyl] butanedioate
  参考文献：
  名称：

  Synthesis of paclitaxel (docetaxel) / 2-deacetoxytaxinine J dimers

  摘要：

  Starting from taxanes available in multigram amounts from widespread ornamental yews (10-deacetylbaccatin III (4) and 2'-deacetoxyaustrospicatine (5)), two dimeric taxoids (3a, 3b) with potential dual target specificity (beta-tubulin and P-gp) were synthesised. Both compounds lacked significant cytotoxicity, though 3b retained a strong activity in the tubulin depolimerisation assay. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00290-2
• 作为产物：
  描述：

  2'-deacetoxyaustrospicatine 在 4-二甲氨基吡啶 、 lithium hydroxide 、 盐酸羟胺 、 sodium acetate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 38.5h， 生成 4-O-[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,15-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-12-yl] 1-O-[(1R,3R,5S,7S,8S,9R,10R,13S)-7,9,10-triacetyloxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-tricyclo[9.3.1.03,8]pentadec-11-enyl] butanedioate
  参考文献：
  名称：

  Synthesis of paclitaxel (docetaxel) / 2-deacetoxytaxinine J dimers

  摘要：

  Starting from taxanes available in multigram amounts from widespread ornamental yews (10-deacetylbaccatin III (4) and 2'-deacetoxyaustrospicatine (5)), two dimeric taxoids (3a, 3b) with potential dual target specificity (beta-tubulin and P-gp) were synthesised. Both compounds lacked significant cytotoxicity, though 3b retained a strong activity in the tubulin depolimerisation assay. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00290-2