| 876716-86-8

• CAS: 876716-86-8
• 化学式: C₅₂H₇₁NO₁₄Si
• 分子量: 962.22
• InChiKey: ODXVARZURMEWOZ-DXTHPMJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.03
• 重原子数：
  68.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  210.29
• 氢给体数：
  3.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 戴斯-马丁氧化剂 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 二乙二醇二甲醚 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Single-site chemical modification at C10 of the baccatin III core of paclitaxel and Taxol C reduces P-glycoprotein interactions in bovine brain microvessel endothelial cells

  摘要：

  A single-site modification of paclitaxel analogs at the C10 position on the baccatin III core that reduces interaction with P-glycoprotein in bovine brain microvessel endothelial cells is described. Modification and derivatization of the C10 po\sition were carried out using a substrate controlled hydride addition to a key C9 and C10 diketone intermediate. The analogs were tested for tubulin assembly and cytotoxicity, and were shown to retain potency similar to paclitaxel. P-glycoprotein interaction was examined using a rhodamine assay and it was found that simple hydrolysis or epimerization of the C10 acetate of paclitaxel and Taxol C can reduce interaction with the P-glycoprotein transporter that may allow for increased permeation of taxanes into the brain. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.063
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 紫杉醇 C 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Single-site chemical modification at C10 of the baccatin III core of paclitaxel and Taxol C reduces P-glycoprotein interactions in bovine brain microvessel endothelial cells

  摘要：

  A single-site modification of paclitaxel analogs at the C10 position on the baccatin III core that reduces interaction with P-glycoprotein in bovine brain microvessel endothelial cells is described. Modification and derivatization of the C10 po\sition were carried out using a substrate controlled hydride addition to a key C9 and C10 diketone intermediate. The analogs were tested for tubulin assembly and cytotoxicity, and were shown to retain potency similar to paclitaxel. P-glycoprotein interaction was examined using a rhodamine assay and it was found that simple hydrolysis or epimerization of the C10 acetate of paclitaxel and Taxol C can reduce interaction with the P-glycoprotein transporter that may allow for increased permeation of taxanes into the brain. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.063

文献信息

• <i>N</i>-Methylation of the C3′ Amide of Taxanes: Synthesis of <i>N</i>-Methyltaxol C and <i>N</i>-Methylpaclitaxel
  作者：Hari K. R. Santhapuram、Apurba Datta、Oliver E. Hutt、Gunda I. Georg

  DOI：10.1021/jo800173h

  日期：2008.6.1

  A method has been developed for the methylation of the C3' amide of taxol C and paclitaxel. Taxol C and paclitaxel were sequentially silylated at the 2', 7, and 1-hydroxyl groups with tert-butyldimethylsilyl chloride, triethylsilyl chloride, and dimethylsilyl chloride, respectively. Subsequent reaction with potassium tert-butoxide and methyl iodide provided the corresponding N-methylated taxane derivatives. Removal of the silyl protecting groups furnished N-methyltaxol C and N-methylpaclitaxel.