4-((1E,5Z)-(S)-6-Iodo-2-methyl-3,8-bis-triethylsilanyloxy-octa-1,5-dienyl)-2-methyl-thiazole | 477192-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-((1E,5Z)-(S)-6-Iodo-2-methyl-3,8-bis-triethylsilanyloxy-octa-1,5-dienyl)-2-methyl-thiazole
• 英文别名: triethyl-[(3Z,6S,7E)-3-iodo-7-methyl-8-(2-methyl-1,3-thiazol-4-yl)-6-triethylsilyloxyocta-3,7-dienoxy]silane
• CAS: 477192-56-6
• 化学式: C₂₅H₄₆INO₂SSi₂
• 分子量: 607.787
• InChiKey: YBRPMJWEKXWOOF-MXBAIUHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.37
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((1E,5Z)-(S)-6-Iodo-2-methyl-3,8-bis-triethylsilanyloxy-octa-1,5-dienyl)-2-methyl-thiazole 在 吡啶 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.17h， 生成 [(3Z,6S,7E)-3-iodo-7-methyl-8-(2-methyl-1,3-thiazol-4-yl)-6-triethylsilyloxyocta-3,7-dienyl] 2,2,2-trichloroethyl carbonate
  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：

  (Z)-(S)-3,8-Dihydroxy-6-iodo-oct-5-en-2-one 在 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 4-((1E,5Z)-(S)-6-Iodo-2-methyl-3,8-bis-triethylsilanyloxy-octa-1,5-dienyl)-2-methyl-thiazole
  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