2-[(2S,4E,9S,10S,11R,14S)-10-hydroxy-9,11,13,13-tetramethyl-2-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-12,16-dioxo-14-triethylsilyloxy-1-oxacyclohexadec-4-en-5-yl]acetaldehyde | 359014-40-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 2-[(2S,4E,9S,10S,11R,14S)-10-hydroxy-9,11,13,13-tetramethyl-2-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-12,16-dioxo-14-triethylsilyloxy-1-oxacyclohexadec-4-en-5-yl]acetaldehyde
• CAS: 359014-40-7
• 化学式: C₃₄H₅₅NO₆SSi
• 分子量: 633.965
• InChiKey: ITNHMHPMXYSUOC-FJBWHNNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.86
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[(2S,4E,9S,10S,11R,14S)-10-hydroxy-9,11,13,13-tetramethyl-2-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-12,16-dioxo-14-triethylsilyloxy-1-oxacyclohexadec-4-en-5-yl]acetaldehyde 在 三氟甲磺酸三甲基硅酯 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.83h， 生成 26-(1,3-dioxolanyl)-12,13-desoxyepothilone B
  参考文献：
  名称：

  Probing the SAR of dEpoB via Chemical Synthesis:  A Total Synthesis Evaluation of C26-(1,3-dioxolanyl)-12,13-desoxyepothilone B

  摘要：

  A practical total synthesis of 26-(1,3-dioxolanyl)-12,13-desoxyepothilone B (26-dioxolanyl dEpoB) was accomplished in a highly convergent manner. A novel sequence was developed to produce the vinyl iodide segment 17 in high enantiomeric excess, which was used in a key B-alkyl Suzuki merger. Subsequently, a Yamaguchi macrocyclization formed the core lactone, while a selective oxidation and a late stage Noyori acetalization incorporated the dioxolane functionality. Sufficient amounts of synthetic 26-dioxolane dEpoB were produced using this sequence for an in vivo analysis in mice containing xenograft CCRF-CEM tumors.

  DOI：

  10.1021/jo020180q
• 作为产物：
  描述：

  t-butyl (3S,6R,7S,8S)-5-oxo-3-triethylsilanoxy-4,4,6,8-tetramethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoate 在 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 三苯胂 、 碘苯二乙酸 、 三乙基硅基三氟甲磺酸酯 、 caesium carbonate 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 51.42h， 生成 2-[(2S,4E,9S,10S,11R,14S)-10-hydroxy-9,11,13,13-tetramethyl-2-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-12,16-dioxo-14-triethylsilyloxy-1-oxacyclohexadec-4-en-5-yl]acetaldehyde
  参考文献：
  名称：

  Probing the SAR of dEpoB via Chemical Synthesis:  A Total Synthesis Evaluation of C26-(1,3-dioxolanyl)-12,13-desoxyepothilone B

  摘要：

  A practical total synthesis of 26-(1,3-dioxolanyl)-12,13-desoxyepothilone B (26-dioxolanyl dEpoB) was accomplished in a highly convergent manner. A novel sequence was developed to produce the vinyl iodide segment 17 in high enantiomeric excess, which was used in a key B-alkyl Suzuki merger. Subsequently, a Yamaguchi macrocyclization formed the core lactone, while a selective oxidation and a late stage Noyori acetalization incorporated the dioxolane functionality. Sufficient amounts of synthetic 26-dioxolane dEpoB were produced using this sequence for an in vivo analysis in mice containing xenograft CCRF-CEM tumors.

  DOI：

  10.1021/jo020180q

文献信息

• Probing the SAR of dEpoB via Chemical Synthesis:  A Total Synthesis Evaluation of C26-(1,3-dioxolanyl)-12,13-desoxyepothilone B
  作者：Mark D. Chappell、Christina R. Harris、Scott D. Kuduk、Aaron Balog、Zhicai Wu、Fei Zhang、Chul Bom Lee、Shawn J. Stachel、Samuel J. Danishefsky、Ting-Chao Chou、Yongbiao Guan

  DOI：10.1021/jo020180q

  日期：2002.11.1

  A practical total synthesis of 26-(1,3-dioxolanyl)-12,13-desoxyepothilone B (26-dioxolanyl dEpoB) was accomplished in a highly convergent manner. A novel sequence was developed to produce the vinyl iodide segment 17 in high enantiomeric excess, which was used in a key B-alkyl Suzuki merger. Subsequently, a Yamaguchi macrocyclization formed the core lactone, while a selective oxidation and a late stage Noyori acetalization incorporated the dioxolane functionality. Sufficient amounts of synthetic 26-dioxolane dEpoB were produced using this sequence for an in vivo analysis in mice containing xenograft CCRF-CEM tumors.