6-α-hydroxy-2'-O-triethylsilyl-7-α-paclitaxel | 200568-20-3

• 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: 6-α-hydroxy-2'-O-triethylsilyl-7-α-paclitaxel
• 英文别名: [(1S,2S,3R,4S,7R,8S,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-triethylsilyloxypropanoyl]oxy-1,8,9-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 200568-20-3
• 化学式: C₅₃H₆₅NO₁₅Si
• 分子量: 984.182
• InChiKey: LOQSURQHPACERW-QLXUGJMXSA-N

物化性质

• 沸点：
  980.2±65.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  70
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.51
• 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：

  6-α-hydroxy-2'-O-triethylsilyl-7-α-paclitaxel 在 sodium hypochlorite 、 4-hydroxy-TEMPO benzoate 、 potassium bromide 作用下， 生成 6-oxo-2'-O-triethylsilyl-7-α-paclitaxel
  参考文献：
  名称：

  Stereospecific synthesis of the major human metabolite of paclitaxel

  摘要：

  The stereospecific synthesis of 6-alpha-hydroxy paclitaxel 10, the major human metabolite of paclitaxel, is described. The 6,7-alpha-diol 4, obtained from paclitaxel, is converted to the 6,7-beta-cyclic sulfate followed by nitrate addition and reduction to afford the title compound. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00707-3
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 6-α-hydroxy-2'-O-triethylsilyl-7-α-paclitaxel
  参考文献：
  名称：

  Stereospecific synthesis of the major human metabolite of paclitaxel

  摘要：

  The stereospecific synthesis of 6-alpha-hydroxy paclitaxel 10, the major human metabolite of paclitaxel, is described. The 6,7-alpha-diol 4, obtained from paclitaxel, is converted to the 6,7-beta-cyclic sulfate followed by nitrate addition and reduction to afford the title compound. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00707-3

文献信息

• Synthesis of metabolically blocked paclitaxel analogues
  作者：Mark D. Wittman、Thomas J. Altstadt、Craig Fairchild、Stephen Hansel、Kathy Johnston、John F. Kadow、Byron H. Long、William C. Rose、Dolatrai M. Vyas、Mu-Jen Wu、Mary E. Zoeckler

  DOI：10.1016/s0960-894x(01)00066-x

  日期：2001.3

  The stereospecific syntheses of the metabolically blocked 6-alpha -F, Cl, Br paclitaxel, and 6-alpha -F-10-acetyldocetaxel are described and in vitro and in vivo activity is presented. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Stereospecific synthesis of 7-deoxy-6-hydroxy paclitaxel
  作者：Mark D. Wittman、Thomas J. Alstadt、John F. Kadow、Dolatrai M. Vyas、Kathy Johnson、Craig Fairchild、Byron Long

  DOI：10.1016/s0040-4039(99)00864-3

  日期：1999.7

  The synthetic transposition of the 7-hydroxyl group of paclitaxel to the 6-position is described. The route presented prepares both the 6-alpha- and beta-isomers stereospecifically. The key step of this transposition involves the stereoselective reduction of the 6,7-alpha-thiocarbonate using tributylgermanium hydride. (C) 1999 Elsevier Science Ltd. All rights reserved.