(1S,5S,6R,7S,8S,10S,11S,13R)-8-bromo-7-hydroxy-11,15,18,18-tetramethyl-3,12,16-trioxo-10,13-bis(triethylsilyloxy)-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-ene-7-carbaldehyde | 194720-24-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: (1S,5S,6R,7S,8S,10S,11S,13R)-8-bromo-7-hydroxy-11,15,18,18-tetramethyl-3,12,16-trioxo-10,13-bis(triethylsilyloxy)-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-ene-7-carbaldehyde
• CAS: 194720-24-6
• 化学式: C₃₃H₅₃BrO₉Si₂
• 分子量: 729.853
• InChiKey: KAMYZESICATVNI-GXSZRXJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S,5S,6R,7S,8S,10S,11S,13R)-8-bromo-7-hydroxy-11,15,18,18-tetramethyl-3,12,16-trioxo-10,13-bis(triethylsilyloxy)-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-ene-7-carbaldehyde 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium cyanoborohydride 、 N,N'-二环己基碳二亚胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 甲苯 、 乙腈 为溶剂， 反应 12.17h， 生成 C₇₀H₉₄N₂O₁₄Si₂
  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：

  (1S,5S,6R,7S,8S,10S,11S,13R,16S)-8-bromo-7,16-dihydroxy-7-(hydroxymethyl)-11,15,18,18-tetramethyl-10,13-bis(triethylsilyloxy)-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-ene-3,12-dione 在 三氟乙酸酐 作用下， 以 二甲基亚砜 为溶剂， 反应 0.75h， 以82%的产率得到(1S,5S,6R,7S,8S,10S,11S,13R)-8-bromo-7-hydroxy-11,15,18,18-tetramethyl-3,12,16-trioxo-10,13-bis(triethylsilyloxy)-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-ene-7-carbaldehyde
  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