(1S,2S,3R,4S,7R,9S,10S,12R,15S)-1,2,4-trihydroxy-10,14,17,17-tetramethyl-9,12,15-tris(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-one | 194720-20-2

• 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: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-1,2,4-trihydroxy-10,14,17,17-tetramethyl-9,12,15-tris(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-one
• CAS: 194720-20-2
• 化学式: C₃₈H₇₂O₈Si₃
• 分子量: 741.241
• InChiKey: CHTGDKZPSKJQBM-OUNJFFHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.73
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  三光气 、 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-1,2,4-trihydroxy-10,14,17,17-tetramethyl-9,12,15-tris(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-one 以 吡啶 、 二氯甲烷 为溶剂， 反应 0.25h， 以92%的产率得到(1S,5S,6R,7S,10R,12S,13S,15R,18S)-7-hydroxy-13,17,20,20-tetramethyl-12,15,18-tris(triethylsilyloxy)-2,4,9-trioxapentacyclo[14.3.1.01,5.06,13.07,10]icos-16-ene-3,14-dione
  参考文献：
  名称：

  Synthesis and Biological Evaluation of D-Ring-Modified Taxanes:¹  5(20)-Azadocetaxel Analogs

  摘要：

  Two 5(20)-aza analogs of docetaxel, N-20-benzyl-5(20)-azadocetaxel (5) and 5(20)-azadocetaxel (6), have been synthesized from 10-deacetylbaccatin III, The key steps of this synthesis involved the direct introduction of a C-5 leaving group while ring opening and the intramolecular nucleophilic attack of the C-20 amino group at C-5. Both compounds were inactive on the in vitro cytotoxic assay, and only the azadocetaxel 6 retains an antitubulin activity, but 16 times less than docetaxel.

  DOI：

  10.1021/jo9706842
• 作为产物：
  描述：

  10-脱乙酰基巴卡丁 III 在 咪唑 、 红铝 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.42h， 生成 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-1,2,4-trihydroxy-10,14,17,17-tetramethyl-9,12,15-tris(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of D-Ring-Modified Taxanes:¹  5(20)-Azadocetaxel Analogs

  摘要：

  Two 5(20)-aza analogs of docetaxel, N-20-benzyl-5(20)-azadocetaxel (5) and 5(20)-azadocetaxel (6), have been synthesized from 10-deacetylbaccatin III, The key steps of this synthesis involved the direct introduction of a C-5 leaving group while ring opening and the intramolecular nucleophilic attack of the C-20 amino group at C-5. Both compounds were inactive on the in vitro cytotoxic assay, and only the azadocetaxel 6 retains an antitubulin activity, but 16 times less than docetaxel.

  DOI：

  10.1021/jo9706842