2-[(1'R,2'S,4'S)-2',4'-di(tert-butyldimethyl-silyloxy)-1'-methyl-5'-hexynyl]-4-thiazole carboxylic acid ethyl ester | 1196718-59-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[(1'R,2'S,4'S)-2',4'-di(tert-butyldimethyl-silyloxy)-1'-methyl-5'-hexynyl]-4-thiazole carboxylic acid ethyl ester
• 英文别名: ethyl 2-[(2R,3S,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]hept-6-yn-2-yl]-1,3-thiazole-4-carboxylate
• CAS: 1196718-59-8
• 化学式: C₂₅H₄₅NO₄SSi₂
• 分子量: 511.874
• InChiKey: MYLCOYRQYYNDGW-SBHAEUEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(1'R,2'S,4'S)-2',4'-di(tert-butyldimethyl-silyloxy)-1'-methyl-5'-hexynyl]-4-thiazole carboxylic acid ethyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 三正丁基氢锡 、 碘 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到2-[(1'R,2'S,4'S)-2',4'-di-(tert-butyldimethyl-silyloxy)-6'-iodo-1'-methyl-(E)-5'-hexenyl]-4-thiazole carboxylic acid ethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of the C1–C12 fragment of the thuggacins

  摘要：

  A concise asymmetric synthesis of the C1-C12 fragment of the antibacterial natural product thuggacins has been achieved. The stereochemistry of this fragment was established efficiently via stereoselective reduction and Evans-aldol condensation. Hanztsch's method and a Horner-Wadsworth-Emmnons reaction were employed for thiazole formation and the construction of the E-alpha,beta-unsaturated double bond. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.015
• 作为产物：
  描述：

  2-[(1'R,2'S,4'S)-2',4'-di(tert-butyldimethyl-silyloxy)-1'-methyl-6'-trimethylsilyl-5'-hexynyl]-4-thiazolecarboxylic acid ethyl ester 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到2-[(1'R,2'S,4'S)-2',4'-di(tert-butyldimethyl-silyloxy)-1'-methyl-5'-hexynyl]-4-thiazole carboxylic acid ethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of the C1–C12 fragment of the thuggacins

  摘要：

  A concise asymmetric synthesis of the C1-C12 fragment of the antibacterial natural product thuggacins has been achieved. The stereochemistry of this fragment was established efficiently via stereoselective reduction and Evans-aldol condensation. Hanztsch's method and a Horner-Wadsworth-Emmnons reaction were employed for thiazole formation and the construction of the E-alpha,beta-unsaturated double bond. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.015

文献信息

• Stereoselective synthesis of the C1–C12 fragment of the thuggacins
  作者：Shoubin Tang、Zhengshuang Xu、Tao Ye

  DOI：10.1016/j.tetasy.2009.08.015

  日期：2009.9

  A concise asymmetric synthesis of the C1-C12 fragment of the antibacterial natural product thuggacins has been achieved. The stereochemistry of this fragment was established efficiently via stereoselective reduction and Evans-aldol condensation. Hanztsch's method and a Horner-Wadsworth-Emmnons reaction were employed for thiazole formation and the construction of the E-alpha,beta-unsaturated double bond. (C) 2009 Elsevier Ltd. All rights reserved.