[(1E,3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-yl] (3S,6R,7S,8S,9R)-3-[tert-butyl(dimethyl)silyl]oxy-4,4,6,8,9,12-hexamethyl-5-oxo-7-triethylsilyloxytridec-12-enoate | 1469891-38-0

• 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: [(1E,3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-yl] (3S,6R,7S,8S,9R)-3-[tert-butyl(dimethyl)silyl]oxy-4,4,6,8,9,12-hexamethyl-5-oxo-7-triethylsilyloxytridec-12-enoate
• CAS: 1469891-38-0
• 化学式: C₄₂H₇₅NO₅SSi₂
• 分子量: 762.298
• InChiKey: FWRUFKKHPZIBBP-RRHGSPHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.37
• 重原子数：
  51
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1E,3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-yl] (3S,6R,7S,8S,9R)-3-[tert-butyl(dimethyl)silyl]oxy-4,4,6,8,9,12-hexamethyl-5-oxo-7-triethylsilyloxytridec-12-enoate 在 Hoveyda-Grubbs catalyst second generation 、 三氟乙酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 (4S,7R,8S,9S,10R,13E,16S)-4,8-dihydroxy-5,5,7,9,10,13-hexamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
  参考文献：
  名称：

  Epothilone D and its 9-Methyl analogues: Combinatorial syntheses, conformation, and biological activities

  摘要：

  Epothilone D (Epo D) and its 9-Methyl conformational analogues were synthesized through a highly efficient combinatorial approach. The fragment E was synthesized in 11 total steps with 6 longest linear steps, and each aldehyde B was prepared via a 3-step sequence. Starting from the common precursor E and a suitable aldehydes B, each target molecule were obtained in only 4 steps. The 9-(S)-epo D and 9-(R)-epo D demonstrated significant difference in inhibition activities against cancer cell lines and in conformational analysis. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.003
• 作为产物：
  描述：

  (S)-3-((tert-butyldimethylsilyl)oxy)-4,4-dimethyl-5-oxoheptanoic acid 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 四氯化钛 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 生成 [(1E,3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-yl] (3S,6R,7S,8S,9R)-3-[tert-butyl(dimethyl)silyl]oxy-4,4,6,8,9,12-hexamethyl-5-oxo-7-triethylsilyloxytridec-12-enoate
  参考文献：
  名称：

  Epothilone D and its 9-Methyl analogues: Combinatorial syntheses, conformation, and biological activities

  摘要：

  Epothilone D (Epo D) and its 9-Methyl conformational analogues were synthesized through a highly efficient combinatorial approach. The fragment E was synthesized in 11 total steps with 6 longest linear steps, and each aldehyde B was prepared via a 3-step sequence. Starting from the common precursor E and a suitable aldehydes B, each target molecule were obtained in only 4 steps. The 9-(S)-epo D and 9-(R)-epo D demonstrated significant difference in inhibition activities against cancer cell lines and in conformational analysis. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.003

文献信息

• Epothilone D and its 9-Methyl analogues: Combinatorial syntheses, conformation, and biological activities
  作者：Feng Sang、Peng Feng、Jie Chen、Yahui Ding、Xiyan Duan、Jiadai Zhai、Xiaoyan Ma、Bin Zhang、Quan Zhang、Jianping Lin、Yue Chen

  DOI：10.1016/j.ejmech.2013.08.003

  日期：2013.10

  Epothilone D (Epo D) and its 9-Methyl conformational analogues were synthesized through a highly efficient combinatorial approach. The fragment E was synthesized in 11 total steps with 6 longest linear steps, and each aldehyde B was prepared via a 3-step sequence. Starting from the common precursor E and a suitable aldehydes B, each target molecule were obtained in only 4 steps. The 9-(S)-epo D and 9-(R)-epo D demonstrated significant difference in inhibition activities against cancer cell lines and in conformational analysis. (C) 2013 Elsevier Masson SAS. All rights reserved.