紫杉醇杂质F | 153083-53-5

• 物质功能分类: 天然产物 - 萜类
• 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: 紫杉醇杂质F
• 英文名称: N-methyl-taxol C
• 英文别名: N-methyltaxol C；N-methyltaxol；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-[hexanoyl(methyl)amino]-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: 153083-53-5
• 化学式: C₄₇H₅₉NO₁₄
• 分子量: 861.984
• InChiKey: LJTMOSWWGSCCPR-AMMYIWEDSA-N

物化性质

• 沸点：
  909.8±65.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  62
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  213
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  N-methyl-2'-tert-butyldimethylsilyl-7-triethylsilyl-taxol C 在 吡啶 、 氟化氢吡啶 作用下， 反应 18.0h， 以97%的产率得到紫杉醇杂质F
  参考文献：
  名称：

  N-Methylation of the C3′ Amide of Taxanes: Synthesis of N-Methyltaxol C and N-Methylpaclitaxel

  摘要：

  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.

  DOI：

  10.1021/jo800173h

文献信息

• [EN] METHODS AND COMPOSITIONS FOR CONVERTING TAXANE AMIDES TO PACLITAXEL OR OTHER TAXANES<br/>[FR] PROCEDES ET COMPOSITIONS POUR TRANSFORMER DES AMIDES DE TAXANE EN PACLITAXEL OU EN AUTRES TAXANES
  申请人：NATURAL PHARMACEUTICALS INC

  公开号：WO2004013096A3

  公开（公告）日：2004-06-17
• <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.