2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester | 646502-75-2

• 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: 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester
• CAS: 646502-75-2
• 化学式: C₆₂H₈₇NO₁₄Si₂
• 分子量: 1126.54
• InChiKey: RHGLRZFXGQHNHP-KELVIHEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  79.0
• 可旋转键数：
  18.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  182.66
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以86%的产率得到[(1S,2S,3S,4S,7S,8S,10R,13S)-4-acetyloxy-1,7,10-trihydroxy-13-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-8,12,15,15-tetramethyl-9-oxo-2-tricyclo[9.3.1.03,8]pentadec-11-enyl] benzoate
  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：

  (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 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 环己烷 、 甲苯 为溶剂， 反应 4.66h， 生成 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester
  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