(3aS,8R,9aS,10S,12S,13R,13aR,13bS)-12-bromo-6,9a,14,14-tetramethyl-2,5,9-trioxo-8,10-bis((triethylsilyl)oxy)-5,8,9,9a,10,11,12,13,13a,13b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13-yl acetate | 646502-69-4

• 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: (3aS,8R,9aS,10S,12S,13R,13aR,13bS)-12-bromo-6,9a,14,14-tetramethyl-2,5,9-trioxo-8,10-bis((triethylsilyl)oxy)-5,8,9,9a,10,11,12,13,13a,13b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13-yl acetate
• CAS: 646502-69-4
• 化学式: C₃₄H₅₅BrO₉Si₂
• 分子量: 743.88
• InChiKey: TVBWUEDSWVQVIJ-WKONVKRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.66
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3aS,8R,9aS,10S,12S,13R,13aR,13bS)-12-bromo-6,9a,14,14-tetramethyl-2,5,9-trioxo-8,10-bis((triethylsilyl)oxy)-5,8,9,9a,10,11,12,13,13a,13b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13-yl acetate 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以88%的产率得到
  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 吡啶 、 lead(IV) acetate 、 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 、 甲苯 、 乙腈 为溶剂， 反应 6.17h， 生成 (3aS,8R,9aS,10S,12S,13R,13aR,13bS)-12-bromo-6,9a,14,14-tetramethyl-2,5,9-trioxo-8,10-bis((triethylsilyl)oxy)-5,8,9,9a,10,11,12,13,13a,13b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13-yl acetate
  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