2'-O-(叔-丁基二甲基硅烷基)紫杉醇7-O-三氟甲烷磺酸酯 | 165065-01-0

• 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
• 中文名称: 2'-O-(叔-丁基二甲基硅烷基)紫杉醇7-O-三氟甲烷磺酸酯
• 英文名称: 2'-O-(t-butyldimethylsilyl)-7β-O-trifluoromethanesulfonyl-paclitaxel
• 英文别名: 2'-O-(t-butyldimethylsilyl)-7β-O-trifluoromethanesulfonylpaclitaxel；2'-(t-butyldimethylsilyl)paclitaxel 7-O-triflate；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-(trifluoromethylsulfonyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 165065-01-0
• 化学式: C₅₄H₆₄F₃NO₁₆SSi
• 分子量: 1100.25
• InChiKey: HCWLKEZRCWJKHE-HYWITDEOSA-N

物化性质

• 沸点：
  982.6±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)：
  7.64
• 重原子数：
  76
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  242
• 氢给体数：
  2
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2'-O-(叔-丁基二甲基硅烷基)紫杉醇7-O-三氟甲烷磺酸酯 在 L-1,4-二硫代苏糖醇 、 碳酸氢钠 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 45.0h， 生成 2'-O-(t-butyldimethylsilyloxy)-7-deoxy-7α-thiopaclitaxel
  参考文献：
  名称：

  受天然化学连接启发的选择性S-脱乙酰化：糖基硫醇和药物巯基类似物的实用合成

  摘要：

  通过在温和的碱性条件下进行简单的硫代酯基转移，即可实现高效的选择性S-脱乙酰基作用。

  DOI：

  10.1039/c5gc00084j
• 作为产物：
  描述：

  三氟甲烷磺酰氯 、 2'-O-(叔-丁基二甲基硅烷基)紫杉醇 在 4-二甲氨基吡啶 作用下， 反应 2.0h， 生成 2'-O-(叔-丁基二甲基硅烷基)紫杉醇7-O-三氟甲烷磺酸酯
  参考文献：
  名称：

  Synthesis and biological evaluation of paclitaxel analogs modified in ring C

  摘要：

  Both 7-deoxy-7 alpha-azidopaclitaxel (6) and 7-deoxy-Delta(6,7)-paclitaxel (4) can be prepared from paclitaxel-7-0-triflate (2b). Oxidation of 7-deoxy-Delta(6,7)-paclitaxel with dioxirane yields the epoxide 7, while oxidation with osmium tetroxide yields 6 alpha-hydroxy-7-epipaclitaxel (9), and acylation of this gives the 6 alpha-acyloxy-7-epipaclitaxel derivatives 11a-d. No compound was as effective at promoting tubulin assembly as paclitaxel, but most stabilized polymer as well as or better than paclitaxel. Compounds 4, 6, 7, 9, and 11d differed little from paclitaxel in their cytotoxicity for human Burkitt lymphoma CA46 cells.

  DOI：

  10.1016/0040-4039(95)00431-b

文献信息

• Synthesis of 7β-Sulfur Analogues of Paclitaxel Utilizing a Novel Epimerization of the 7α-Thiol Group
  作者：Harold Mastalerz、Guifen Zhang、John Kadow、Craig Fairchild、Byron Long、Dolatrai M. Vyas

  DOI：10.1021/ol015727m

  日期：2001.5.1

  [GRAPHICS]90 degreesCPaclitaxel analogues with a sulfur group at the 7 beta position were required for SAR studies, Attempts to generate these compounds by displacing a 7 alpha leaving group with sulfur nucleophiles were unsuccessful. Instead, these compounds were successfully prepared from a 7 beta -thiol intermediate that was obtained by a base-catalyzed epimerization of the 7 alpha -thiol derivative. The epimerization presumably proceeds through a thioaldehyde intermediate and exhibits the opposite stereochemical preference of its oxygen counterpart.
• Paclitaxel analogs modified in ring C: Synthesis and biological evaluation
  作者：Xian Liang、David G.I. Kingston、Byron H. Long、Craig A. Fairchild、Kathy A. Johnston

  DOI：10.1016/s0040-4020(97)00074-4

  日期：1997.3

  Lead tetracetate oxidation of 6 alpha-hydroxy-7-epi-paclitaxel leads to C-nor-paclitaxel and C-seco-paclitaxel derivatives. Tetrapropylammonium permthenate (TPAP) oxidation of a 6 alpha-hydroxy-7-epi-paclitaxel derivative leads to a 6-formyl-C-nor-paclitaxel derivative. Reaction of a 6 alpha-O-trifluoromethanesulfonyl-7-epi-paclitaxel derivative with DMAP yields a 20-O-acetyl-4-deacetyl-5,6-dehydro-6-formyl-C-nor-paclitaxel derivative. C-nor-paclitaxel analogs are less active than paclitaxel. (C) 1997 Elsevier Science Ltd.