methyl (E,3S)-3-hydroxy-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-enoate | 868158-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl (E,3S)-3-hydroxy-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-enoate
• CAS: 868158-80-9
• 化学式: C₁₁H₁₅NO₃S
• 分子量: 241.311
• InChiKey: GWDAZMSXIGVJAZ-QBBOHKLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  87.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E,3S)-3-hydroxy-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-enoate 在 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 1.0h， 生成 (E,3S)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)-3-(oxan-2-yloxy)pent-4-enal
  参考文献：
  名称：

  A cyclopropanol approach to the synthesis of the C13–C21 fragment of epothilones from diethyl (S)-malate

  摘要：

  A convenient new approach to the synthesis of the C13-C21 epothilone fragment using the cyclopropanation of the ethoxycarbonyl groups in O-THP protected diethyl (S)-malate with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide followed by site-selective cyclopropane cleavage as the key steps has been performed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.075
• 作为产物：
  描述：

  在 potassium tert-butylate 、 4-甲基苯磺酸吡啶 作用下， 以 叔丁醇 为溶剂， 反应 3.5h， 生成 methyl (E,3S)-3-hydroxy-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-enoate
  参考文献：
  名称：

  A cyclopropanol approach to the synthesis of the C13–C21 fragment of epothilones from diethyl (S)-malate

  摘要：

  A convenient new approach to the synthesis of the C13-C21 epothilone fragment using the cyclopropanation of the ethoxycarbonyl groups in O-THP protected diethyl (S)-malate with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide followed by site-selective cyclopropane cleavage as the key steps has been performed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.075

文献信息

• Practical syntheses of the C12–C21 epothilone subunit via catalytic asymmetric reductions: Itsuno–Corey oxazaborolidine reduction and asymmetric Noyori hydrogenation
  作者：Emily A Reiff、Sajiv K Nair、B.S Narayan Reddy、Jun Inagaki、John T Henri、Jack F Greiner、Gunda I Georg

  DOI：10.1016/j.tetlet.2004.06.009

  日期：2004.7

  Two practical catalytic asymmetric reductions to introduce the epothilone C15 stereocenter are described (Itsuno-Corey reduction and Noyori hydrogenation). (C) 2004 Elsevier Ltd. All rights reserved.
• A cyclopropanol approach to the synthesis of the C13–C21 fragment of epothilones from diethyl (S)-malate
  作者：Andrei V. Bekish、Vladimir E. Isakov、Oleg G. Kulinkovich

  DOI：10.1016/j.tetlet.2005.08.075

  日期：2005.10

  A convenient new approach to the synthesis of the C13-C21 epothilone fragment using the cyclopropanation of the ethoxycarbonyl groups in O-THP protected diethyl (S)-malate with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide followed by site-selective cyclopropane cleavage as the key steps has been performed. (c) 2005 Elsevier Ltd. All rights reserved.