(1S,5S,6R,8S,10S,11S,13R)-8-bromo-11,15,18,18-tetramethyl-10,13-bis(triethylsilyloxy)-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-ene-3,7,12,16-tetrone | 646502-66-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1S,5S,6R,8S,10S,11S,13R)-8-bromo-11,15,18,18-tetramethyl-10,13-bis(triethylsilyloxy)-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-ene-3,7,12,16-tetrone
• CAS: 646502-66-1
• 化学式: C₃₂H₅₁BrO₈Si₂
• 分子量: 699.827
• InChiKey: GJOXTDBNUPFOLG-LVEJPUKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,5S,6R,8S,10S,11S,13R)-8-bromo-11,15,18,18-tetramethyl-10,13-bis(triethylsilyloxy)-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-ene-3,7,12,16-tetrone 在 吡啶 、 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.17h， 生成
  参考文献：
  名称：

  Deletion of the Oxetane Ring in Docetaxel Analogues:  Synthesis and Biological Evaluation

  摘要：

  [GRAPHICS]Two new docetaxel analogues have been prepared starting from 10-deacetylbaccatin III. Both derivatives lack the oxetane D-ring but possess the 4alpha-acetoxy group, which is important for biological activity. The influence of a more or less constrained C-ring was evaluated by adding, or not adding, a double bond in this ring. Both compounds were found to be equally less active than docetaxel in biological assays.

  DOI：

  10.1021/ol036043c
• 作为产物：
  描述：

  2-debenzoyl-4-deacetyl-5α-bromo-7,10-di(triethylsilyl)-20-hydroxy-13-oxo-D-seco-10-deacetylbaccatin III 1,2 carbonate 在 lead(IV) acetate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以98.8%的产率得到(1S,5S,6R,8S,10S,11S,13R)-8-bromo-11,15,18,18-tetramethyl-10,13-bis(triethylsilyloxy)-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-ene-3,7,12,16-tetrone
  参考文献：
  名称：

  Deletion of the Oxetane Ring in Docetaxel Analogues:  Synthesis and Biological Evaluation

  摘要：

  [GRAPHICS]Two new docetaxel analogues have been prepared starting from 10-deacetylbaccatin III. Both derivatives lack the oxetane D-ring but possess the 4alpha-acetoxy group, which is important for biological activity. The influence of a more or less constrained C-ring was evaluated by adding, or not adding, a double bond in this ring. Both compounds were found to be equally less active than docetaxel in biological assays.

  DOI：

  10.1021/ol036043c