(2R,3S,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methyl-7-trimethylsilyl-6-heptyne-thioamide | 1196718-39-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3S,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methyl-7-trimethylsilyl-6-heptyne-thioamide
• 英文别名: (2R,3S,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-7-trimethylsilylhept-6-ynethioamide
• CAS: 1196718-39-4
• 化学式: C₂₃H₄₉NO₂SSi₃
• 分子量: 487.97
• InChiKey: DNXMYMKZZAEPBA-AQNXPRMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  76.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-溴丙酮酸乙酯 、 (2R,3S,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methyl-7-trimethylsilyl-6-heptyne-thioamide 在 2,6-二甲基吡啶 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以68%的产率得到2-[(1'R,2'S,4'S)-2',4'-di(tert-butyldimethyl-silyloxy)-1'-methyl-6'-trimethylsilyl-5'-hexynyl]-4-thiazolecarboxylic 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：

  (2R,3S,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methyl-7-trimethylsilyl-6-heptynamide 在 劳森试剂 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以72%的产率得到(2R,3S,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methyl-7-trimethylsilyl-6-heptyne-thioamide
  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