7-(triethylsilyl)baccatin III 13- | 155399-27-2

• 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: 7-(triethylsilyl)baccatin III 13-
• 英文别名: 7-(triethylsilyl)baccatin III 13-[N-(benzyloxycarbonyl)-(2R,3S)-3-phenylisoserinate]；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylmethoxycarbonylamino)propanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 155399-27-2
• 化学式: C₄₈H₅₃NO₁₅
• 分子量: 883.947
• InChiKey: XXGITWZCIHRAKS-JBTWBBNCSA-N

物化性质

• 沸点：
  946.6±65.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  64
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  231
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  7-(triethylsilyl)baccatin III 13- 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 5.08h， 生成 N-(4-azido-<3,5-3H>benzoyl)-N-debenzoyltaxol
  参考文献：
  名称：

  Dasgupta; Park; Harriman, Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2976 - 2980

  摘要：

  DOI：
• 作为产物：
  描述：

  3'-N-debenzoyl-3'-N-Troc-7-Troc-paclitaxel 在 碳酸氢钠 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 10.0h， 生成 7-(triethylsilyl)baccatin III 13-
  参考文献：
  名称：

  No Auxiliary, No Byproduct Strategy for Water-Soluble Prodrugs of Taxoids:  Scope and Limitation of O−N Intramolecular Acyl and Acyloxy Migration Reactions

  摘要：

  Since numerous new taxoids active against multidrug resistant (MDR) tumors have been developed and their poor water-solubility is a very real problem in intravenous administration, we have designed and synthesized a series of novel water-soluble taxoid prodrugs (isotaxoids). These prodrugs, a 2'-O-isoform of taxoids, showed promising results with higher water solubility (0.8- 1.1 mg/mL) and proper kinetics for parent drug release by a simple pH-dependent chemical mechanism via O-N intramolecular acyl migration. No additional functional auxiliaries are released during the conversion to parent drugs, which would be an advantage in toxicology and general pharmacology, and the cost for the evaluations of auxiliary units in these fields could be saved in prodrug development. In addition, we demonstrate for the first time the successful application of the O-N intramolecular acyloxy migration reaction in the prodrug design, with the exception of the tert-butyloxycarbonyl group, and that this reaction can be provided with no organic solvent and no side products.

  DOI：

  10.1021/jm049344g

文献信息

• Synthesis of taxol, analogs and intermediates with variable A-nng side chains
  申请人：BRYN MAWR COLLEGE

  公开号：EP1260507A1

  公开（公告）日：2002-11-27

  An efficient protocol for the synthesis of taxol, taxol analogs, and their intermediates is described. The process includes the attachment of the taxol A-ring side chain to baccatin III and for the synthesis of taxol and taxol analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyoloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make taxol, calphalomanninne and various analogs, including photoaffinity labeling candidates.

  本文介绍了一种有效的紫杉醇、紫杉醇类似物及其中间体的合成协议。该过程包括将紫杉醇A环侧链连接到紫杉醇前体baccatin III上，以及用具有可变A环侧链结构的化合物合成紫杉醇和紫杉醇类似物。通过快速高效的酯化反应，将O保护的异丝氨酸和3-苯基异丝氨酸酸与N-苄氧羰基基团连接到7-O保护的baccatin III的C-13羟基上，然后进行去保护-酰化序列，制备紫杉醇、卡法洛曼宁和各种类似物，包括光亲和标记候选物。
• No Auxiliary, No Byproduct Strategy for Water-Soluble Prodrugs of Taxoids:  Scope and Limitation of O−N Intramolecular Acyl and Acyloxy Migration Reactions
  作者：Mariusz Skwarczynski、Youhei Sohma、Mayo Noguchi、Maiko Kimura、Yoshio Hayashi、Yoshio Hamada、Tooru Kimura、Yoshiaki Kiso

  DOI：10.1021/jm049344g

  日期：2005.4.1

  Since numerous new taxoids active against multidrug resistant (MDR) tumors have been developed and their poor water-solubility is a very real problem in intravenous administration, we have designed and synthesized a series of novel water-soluble taxoid prodrugs (isotaxoids). These prodrugs, a 2'-O-isoform of taxoids, showed promising results with higher water solubility (0.8- 1.1 mg/mL) and proper kinetics for parent drug release by a simple pH-dependent chemical mechanism via O-N intramolecular acyl migration. No additional functional auxiliaries are released during the conversion to parent drugs, which would be an advantage in toxicology and general pharmacology, and the cost for the evaluations of auxiliary units in these fields could be saved in prodrug development. In addition, we demonstrate for the first time the successful application of the O-N intramolecular acyloxy migration reaction in the prodrug design, with the exception of the tert-butyloxycarbonyl group, and that this reaction can be provided with no organic solvent and no side products.
• Dasgupta; Park; Harriman, Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2976 - 2980
  作者：Dasgupta、Park、Harriman、Georg、Himes

  DOI：——

  日期：——