2'-epi 3'-epi N-debenzoyl N-tert-butoxycarbonyl taxol | 125354-17-8

• 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'-epi 3'-epi N-debenzoyl N-tert-butoxycarbonyl taxol
• 英文别名: Lemyaxkycobyoj-dvbuqmqdsa-；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2S,3R)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 125354-17-8
• 化学式: C₄₅H₅₅NO₁₅
• 分子量: 849.929
• InChiKey: LEMYAXKYCOBYOJ-DVBUQMQDSA-N

物化性质

• 沸点：
  901.4±65.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  61
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  231
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  (+/-)-cis-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 在 4-二甲氨基吡啶 、 lithium hydroxide 、 ammonium cerium(IV) nitrate 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 10.83h， 生成 2'-epi 3'-epi N-debenzoyl N-tert-butoxycarbonyl taxol
  参考文献：
  名称：

  Synthesis of Docetaxel and Butitaxel Analogues through Kinetic Resolution of Racemic β-Lactams with 7-O-Triethylsilylbaccatin III

  摘要：

  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.

  DOI：

  10.1021/jo061339s

文献信息

• Application of the vicinal oxyamination reaction with asymmetric induction to the hemisynthesis of taxol and analogues
  作者：L. Mangatal、M.-T. Adeline、D. Guénard、F. Guéritte-Voegelein、P. Potier

  DOI：10.1016/s0040-4020(01)81313-2

  日期：1989.1
• MANGATAL, L.;ADELINE, M. -T.;GUENARD, D.;GUERITTE-VOEGELEIN, F.;POTIER, P+, TETRAHEDRON, 45,(1989) N3, C. 4177-4190
  作者：MANGATAL, L.、ADELINE, M. -T.、GUENARD, D.、GUERITTE-VOEGELEIN, F.、POTIER, P+

  DOI：——

  日期：——
• 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.