Carbonic acid (E)-(4S,7R,8S,9S,16S)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-2,6-dioxo-13-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-triethylsilanyloxy-oxacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester | 359014-38-3

• 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: Carbonic acid (E)-(4S,7R,8S,9S,16S)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-2,6-dioxo-13-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-triethylsilanyloxy-oxacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester
• 英文别名: [(4S,7R,8S,9S,13E,16S)-5,5,7,9-tetramethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-2,6-dioxo-13-[2-(2,2,2-trichloroethoxycarbonyloxy)ethyl]-4-triethylsilyloxy-1-oxacyclohexadec-13-en-8-yl] 2,2,2-trichloroethyl carbonate
• CAS: 359014-38-3
• 化学式: C₄₀H₅₉Cl₆NO₁₀SSi
• 分子量: 986.779
• InChiKey: DFQKZXALCFKABA-BTWKFLMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.72
• 重原子数：
  59
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Carbonic acid (E)-(4S,7R,8S,9S,16S)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-2,6-dioxo-13-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-triethylsilanyloxy-oxacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 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
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以0.466 g的产率得到Carbonic acid (E)-(4S,7R,8S,9S,16S)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-2,6-dioxo-13-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-triethylsilanyloxy-oxacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester
  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.