[(1E,3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-yl] (3S)-3-[tert-butyl(dimethyl)silyl]oxy-4,4-dimethyl-5-oxoheptanoate | 1268032-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [(1E,3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-yl] (3S)-3-[tert-butyl(dimethyl)silyl]oxy-4,4-dimethyl-5-oxoheptanoate
• CAS: 1268032-95-6
• 化学式: C₂₆H₄₃NO₄SSi
• 分子量: 493.783
• InChiKey: XJQUAVWRVQPLSH-YJHOGRMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  93.7
• 氢给体数：
  0
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(S)-3-((tert-butyldimethylsilyl)oxy)-4,4-dimethyl-5-oxoheptanoic acid	187283-45-0	C15H30O4Si	302.486

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(1S)-1-[(E)-1-Methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-3-butenyl (3S,6R,7S,8S)-3,7-di-[tert-butyldimethylsilyloxy]-4,4,6,8,12-pentamethyl-5-oxo-12-tridecenoate	197233-39-9	C41H73NO5SSi2	748.271
  ——	[(1E,3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-yl] (3S,6R,7S,8S)-3-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-4,4,6,8,12-pentamethyl-5-oxotridec-12-enoate	1393891-86-5	C35H59NO5SSi	634.009
  ——	[(1E,3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-yl] (3S,6R,7S,8S,9S)-3-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-4,4,6,8,9,12-hexamethyl-5-oxotridec-12-enoate	1268032-98-9	C36H61NO5SSi	648.036
  ——	[(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-7-hydroxy-4,4,6,8,9,12-hexamethyl-5-oxotridec-12-enoate	1268033-09-5	C36H61NO5SSi	648.036
  ——	[(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	C42H75NO5SSi2	762.298
  ——	[(1E,3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-yl] (3S,6R,7S,8S,9S)-3-[tert-butyl(dimethyl)silyl]oxy-4,4,6,8,9,12-hexamethyl-5-oxo-7-triethylsilyloxytridec-12-enoate	1469891-42-6	C42H75NO5SSi2	762.298
  (4S,7R,8S,9S,13Z,16S)-4,8-二-{[叔-丁基(二甲基)硅烷基]氧基}-5,5,7,9,13-五甲基-16-[(E)-1-甲基-2-(2-甲基-1,3-噻唑-4-基)乙烯基]氧代环己癸-13-烯-2,6-二酮	(4S,7R,8S,9S,13Z,16S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxacyclohexadec-13-ene-2,6-dione	189453-35-8	C39H69NO5SSi2	720.218
  ——	(4S,7R,8S,9S,10S,13Z,16S)-4-[tert-butyl(dimethyl)silyl]oxy-5,5,7,9,10,13-hexamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-8-triethylsilyloxy-1-oxacyclohexadec-13-ene-2,6-dione	1469891-43-7	C40H71NO5SSi2	734.244
  ——	(4S,7R,8S,9S,10R,13Z,16S)-4-[tert-butyl(dimethyl)silyl]oxy-5,5,7,9,10,13-hexamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-8-triethylsilyloxy-1-oxacyclohexadec-13-ene-2,6-dione	1469891-39-1	C40H71NO5SSi2	734.244
  ——	(4S,7R,8S,9S,10S,13E,16S)-4-[tert-butyl(dimethyl)silyl]oxy-5,5,7,9,10,13-hexamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-8-triethylsilyloxy-1-oxacyclohexadec-13-ene-2,6-dione	1469891-44-8	C40H71NO5SSi2	734.244

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)-3-[tert-butyl(dimethyl)silyl]oxy-4,4-dimethyl-5-oxoheptanoate 在 2,6-二甲基吡啶 、 Hoveyda-Grubbs catalyst second generation 、 四氯化钛 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 27.0h， 生成 埃博霉素
  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：

  (3S)-3-[((tert-butyl)dimethylsilyl)oxy]-1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.0^1.5]dec-4-yl]-4,4-dimethylheptan-1,5-dione 在 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 双氧水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 26.5h， 生成 [(1E,3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-yl] (3S)-3-[tert-butyl(dimethyl)silyl]oxy-4,4-dimethyl-5-oxoheptanoate
  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.