2-[(1'R,2'S,4'S)-2',4'-di-(tert-butyldimethylsilyloxy)-6'-iodo-1'-methyl-(E)-5'-hexenyl]-4-formylthiazole | 1196718-37-2

• 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-butyldimethylsilyloxy)-6'-iodo-1'-methyl-(E)-5'-hexenyl]-4-formylthiazole
• 英文别名: 2-[(E,2R,3S,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-7-iodohept-6-en-2-yl]-1,3-thiazole-4-carbaldehyde
• CAS: 1196718-37-2
• 化学式: C₂₃H₄₂INO₃SSi₂
• 分子量: 595.733
• InChiKey: QKMNJVHGRUMPFT-XQQQZFNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.18
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  76.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(diethoxyphosphoryl)octanoate 、 2-[(1'R,2'S,4'S)-2',4'-di-(tert-butyldimethylsilyloxy)-6'-iodo-1'-methyl-(E)-5'-hexenyl]-4-formylthiazole 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以74%的产率得到ethyl (2E)-2-[[2-[(E,2R,3S,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-7-iodohept-6-en-2-yl]-1,3-thiazol-4-yl]methylidene]octanoate
  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)-6'-iodo-1'-methyl-(E)-5'-hexenyl]-4-thiazole carboxylic acid ethyl ester 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以84%的产率得到2-[(1'R,2'S,4'S)-2',4'-di-(tert-butyldimethylsilyloxy)-6'-iodo-1'-methyl-(E)-5'-hexenyl]-4-formylthiazole
  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