2'-O-tert-butyldimethylsilyl-7-O-triethylsilyldocetaxel | 220985-01-3

• 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: 2'-O-tert-butyldimethylsilyl-7-O-triethylsilyldocetaxel
• 英文别名: 7-O-triethylsilyl-10-acetyldocetaxel；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1-hydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 220985-01-3
• 化学式: C₅₁H₆₉NO₁₅Si
• 分子量: 964.192
• InChiKey: YQWVNFSEUMSWNO-CEPOORRRSA-N

物化性质

• 沸点：
  908.8±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  68
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  220
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2'-O-tert-butyldimethylsilyl-7-O-triethylsilyldocetaxel 在 双氧水 、 碳酸氢钠 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 多西他赛
  参考文献：
  名称：

  A facile N-debenzoylation of paclitaxel: Conversion of paclitaxel to docetaxel

  摘要：

  An efficient and regioselective method for the N-debenzoylation of paclitaxel has been developed, and has been applied to the conversion of paclitaxel to 10-acetyldocetaxel and to docetaxel. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02221-7
• 作为产物：
  描述：

  2'-benzyloxycarbonyl-7-triethylsilyl taxol 在 4-二甲氨基吡啶 、 magnesium methanolate 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 27.75h， 生成 2'-O-tert-butyldimethylsilyl-7-O-triethylsilyldocetaxel
  参考文献：
  名称：

  A facile N-debenzoylation of paclitaxel: Conversion of paclitaxel to docetaxel

  摘要：

  An efficient and regioselective method for the N-debenzoylation of paclitaxel has been developed, and has been applied to the conversion of paclitaxel to 10-acetyldocetaxel and to docetaxel. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02221-7

文献信息

• Synthesis of Docetaxel and Butitaxel Analogues through Kinetic Resolution of Racemic β-Lactams with 7-<i>O</i>-Triethylsilylbaccatin III
  作者：Haibo Ge、Jared T. Spletstoser、Yan Yang、Margaret Kayser、Gunda I. Georg

  DOI：10.1021/jo061339s

  日期：2007.2.1

  The kinetic resolution of racemic cis-4-phenyl- and cis-4-tert-butyl-3-hydroxy-beta-lactam derivatives with 7-O-triethylsilylbaccatin III yielded paclitaxel and butitaxel analogues with high diastereoselectivity. The results demonstrated that the tert-butyldimethylsilyl protecting group at the C3-hydroxy group of the beta-lactams provided optimum kinetic resolution in comparison with the sterically less demanding triethylsilyl group and the larger triisopropylsilyl group. In addition, it was found that the C4 beta-lactam substituents also influenced diastereoselectivity. The C4 tert-butyl-beta-lactams provided better diastereoselectivity than the corresponding C4 phenyl beta-lactams.