10-deacetoxy-7-deoxypaclitaxel | 150930-88-4

• 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: 10-deacetoxy-7-deoxypaclitaxel
• 英文别名: 7,10-dideoxy taxol；7,10-Dideoxytaxol；[(1S,2S,3R,4S,7R,10R,15S)-4-acetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 150930-88-4
• 化学式: C₄₅H₄₉NO₁₁
• 分子量: 779.884
• InChiKey: MUGRUYNAPBDGDB-AVSUKOOESA-N

物化性质

• 沸点：
  901.5±65.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  57
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  175
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12-(benzoyloxy)-9,11-dihydroxy-4a,8,13,13-tetramethyl-4-(((methylthio)carbonothioyl)oxy)-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 10-deacetoxy-7-deoxypaclitaxel
  参考文献：
  名称：

  轻松合成7,10-二脱氧紫杉醇和7-epi-10-脱氧紫杉醇

  摘要：

  由浆果赤霉素III通过Barton脱氧反应，在4个步骤中制备7，10-二脱氧紫杉醇2。类似地，以高收率从7-表紫杉醇一步制备7-表-10-脱氧紫杉醇3。关键反应是氢化三丁基林介导的乙酸C 10的直接还原。

  DOI：

  10.1016/s0040-4039(00)91810-0

文献信息

• Synthesis and interactions of 7-deoxy-, 10-deacetoxy, and 10-deacetoxy-7-deoxypaclitaxel with NCI/ADR-RES cancer cells and bovine brain microvessel endothelial cells
  作者：Haibo Ge、Veena Vasandani、Jacquelyn K. Huff、Kenneth L. Audus、Richard H. Himes、Anna Seelig、Gunda I. Georg

  DOI：10.1016/j.bmcl.2005.09.043

  日期：2006.1

  7-Deoxypaclitaxel, 10-deacetoxypaclitaxel and 10-deacetoxy-7-deoxypaclitaxel were prepared and evaluated for their ability to promote assembly of tubulin into microtubules, their cytotoxicity against NCI/ADR-RES cells and for their interactions with P-glycoprotein in bovine brain microvessel endothelial cells. The three compounds were essentially equivalent to paclitaxel in cytotoxicity against NCI/ADR-RES cells. They also appeared to interact with P-glycoprotein in the endothelial cells with the two 10-deacetoxy compounds having less interaction than paclitaxel and 7-deoxypaclitaxel. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of 7-deoxy- and 7,10-dideoxytaxol via radical intermediates
  作者：Shu Hui Chen、Stella Huang、Joydeep Kant、Craig Fairchild、Jianmei Wei、Vittorio Farina

  DOI：10.1021/jo00071a002

  日期：1993.9

  7-Deoxytaxol and 7,10-dideoxytaxol were prepared from baccatin III, employing the Barton deoxygenation procedure and the Holton acylation method at C-13.