[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 2,5-dimethoxybenzoate | 564476-28-4

• 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,15S)-4-acetyloxy-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 2,5-dimethoxybenzoate
• CAS: 564476-28-4
• 化学式: C₃₇H₅₄O₁₂Si
• 分子量: 718.914
• InChiKey: HRLIZLXGWWZRII-RUSCNZEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  50.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  167.28
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 2,5-dimethoxybenzoate 在 一水合肼 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 7-(triethylsilyl)-2'-(triisopropylsilyloxy)-3'-dephenyl-3'-(isobutenyl)-2-debenzoyl-2-(2,5-dimethoxybenzoyl)-docetaxel
  参考文献：
  名称：

  Synthesis of potent taxoids for tumor-specific delivery using monoclonal antibodies

  摘要：

  The targeted delivery of taxoids, in the form of taxane-antibody immunoconjugates, requires the preparation of taxoids containing moieties suitable for their conjugation to monoclonal antibodies. A series of taxoids incorporating a disulfide-containing linker at various positions of the taxoid framework have been prepared to investigate the most suitable position for conjugation. A second series of taxoids modified at the C-2 position aimed at increasing the potency of these taxanes has also been prepared. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.027
• 作为产物：
  描述：

  7,10,13-tris(triethylsilyl)-2-debenzoyl-10-deacetylbaccatin III 在 咪唑 、 4-二甲氨基吡啶 、 氟化氢吡啶 、 达卡巴嗪 作用下， 反应 40.0h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 2,5-dimethoxybenzoate
  参考文献：
  名称：

  Synthesis of potent taxoids for tumor-specific delivery using monoclonal antibodies

  摘要：

  The targeted delivery of taxoids, in the form of taxane-antibody immunoconjugates, requires the preparation of taxoids containing moieties suitable for their conjugation to monoclonal antibodies. A series of taxoids incorporating a disulfide-containing linker at various positions of the taxoid framework have been prepared to investigate the most suitable position for conjugation. A second series of taxoids modified at the C-2 position aimed at increasing the potency of these taxanes has also been prepared. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.027

文献信息

• Facile method for synthesizing baccatin III compounds
  申请人：Baloglu Erkan

  公开号：US20050256323A1

  公开（公告）日：2005-11-17

  A process for synthesizing a C-7 protected baccatin III compound represented by formula (A), which comprises reacting a 10-deacetylbaccatin III compound represented by formula (B) with a protecting agent and an acylating agent in the presence of a secondary amine and a nitrogen-containing compound. Also, a process for synthesizing a C-7 protected 10-deacetylbaccatin III compound represented by formula (C), which comprises reacting a 10-deacetylbaccatin III compound represented by formula (B) with a protecting agent in the presence of a secondary amine and a nitrogen-containing compound. In both processes the nitrogen-containing compound is selected from a nitrogen-containing heterocycle or a trialkylamine. When the nitrogen-containing heterocycle is selected, it may be an unsubstituted or a substituted pyridine or an unsubstituted or a substituted pyrazine. When a trialkylamine is selected, it may be, for example, triethylamine or diisopropylethylamine. wherein PG 1 represents the organic residue of the protecting agent, PG 2 represents the organic residue of the acylating agent, and R represents a simple or substituted aryl group or a heterocyclic group.

  一种合成C-7保护的巴卡汀III化合物的方法，其包括在辅助胺和含氮化合物的存在下，将式（B）所表示的10-去乙酰基巴卡汀III化合物与保护试剂和酰化试剂反应。同时，一种合成C-7保护的10-去乙酰基巴卡汀III化合物的方法，其包括在辅助胺和含氮化合物的存在下，将式（B）所表示的10-去乙酰基巴卡汀III化合物与保护试剂反应。在两种方法中，所述的含氮化合物是从含氮杂环或三烷基胺中选择的。当选择含氮杂环时，它可以是未取代或取代的吡啶或未取代或取代的吡嗪。当选择三烷基胺时，它可以是三乙胺或二异丙基乙胺等。其中，PG1表示保护试剂的有机残基，PG2表示酰化试剂的有机残基，R表示简单或取代的芳基或杂环基。