[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-(tert-butylcarbamoyloxy)-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate | 190778-60-0

• 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)-4,12-diacetyloxy-15-[(2R,3S)-3-(tert-butylcarbamoyloxy)-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 190778-60-0
• 化学式: C₄₅H₅₅NO₁₅
• 分子量: 849.929
• InChiKey: XQZTXNCSXJWFJD-DVBUQMQDSA-N

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

• 作为反应物：
  描述：

  [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-(tert-butylcarbamoyloxy)-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate 在 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到iso-docetaxel
  参考文献：
  名称：

  Structure-activity relationships study at the 3′-N position of paclitaxel-part 1: Synthesis and biological evaluation of the 3′-(t)-butylaminocarbonyloxy bearing paclitaxel analogs

  摘要：

  An efficient syntheses of the 3'-N isomeric paclitaxel analogs, 4 and 5, are described. A highly diastereoselective Sharpless asymmetric dihydroxylation reaction is utilized to establish the required (2'R, 3'S) stereochemistry on the C-13 side chain. Both of the 3'-N modified analogs 4 and 5 were found to be cytotoxic in vitro. Analog 4 also displayed comparable in vivo activity to that of paclitaxel in the ip M-109 tumor model. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10142-1
• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙腈 为溶剂， 以81%的产率得到[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-(tert-butylcarbamoyloxy)-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Structure-activity relationships study at the 3′-N position of paclitaxel-part 1: Synthesis and biological evaluation of the 3′-(t)-butylaminocarbonyloxy bearing paclitaxel analogs

  摘要：

  An efficient syntheses of the 3'-N isomeric paclitaxel analogs, 4 and 5, are described. A highly diastereoselective Sharpless asymmetric dihydroxylation reaction is utilized to establish the required (2'R, 3'S) stereochemistry on the C-13 side chain. Both of the 3'-N modified analogs 4 and 5 were found to be cytotoxic in vitro. Analog 4 also displayed comparable in vivo activity to that of paclitaxel in the ip M-109 tumor model. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10142-1

文献信息

• Structure-activity relationships study at the 3′-N position of paclitaxel-part 1: Synthesis and biological evaluation of the 3′-(t)-butylaminocarbonyloxy bearing paclitaxel analogs
  作者：Shu-Hui Chen、May Xue、Stella Huang、Byron H Long、Craig A Fairchild、William C Rose、John F Kadow、Dolatrai Vyas

  DOI：10.1016/s0960-894x(97)10142-1

  日期：1997.12

  An efficient syntheses of the 3'-N isomeric paclitaxel analogs, 4 and 5, are described. A highly diastereoselective Sharpless asymmetric dihydroxylation reaction is utilized to establish the required (2'R, 3'S) stereochemistry on the C-13 side chain. Both of the 3'-N modified analogs 4 and 5 were found to be cytotoxic in vitro. Analog 4 also displayed comparable in vivo activity to that of paclitaxel in the ip M-109 tumor model. (C) 1997 Elsevier Science Ltd.