(2S)-methyl 2-(trifluoromethylsulfonyloxy)-4-(tert-butyldiphenylsilyloxy)butanoate | 1528746-69-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (2S)-methyl 2-(trifluoromethylsulfonyloxy)-4-(tert-butyldiphenylsilyloxy)butanoate
• 英文别名: methyl (2S)-4-[tert-butyl(diphenyl)silyl]oxy-2-(trifluoromethylsulfonyloxy)butanoate
• CAS: 1528746-69-1
• 化学式: C₂₂H₂₇F₃O₆SSi
• 分子量: 504.599
• InChiKey: JBTNFVRBCIMYJS-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S)-methyl 2-(trifluoromethylsulfonyloxy)-4-(tert-butyldiphenylsilyloxy)butanoate 在 potassium carbonate 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 5.5h， 生成 (3R)-methyl 2-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-4-hydroxybutanoate
  参考文献：
  名称：

  Concise total syntheses of heliannuols B and D

  摘要：

  Concise and efficient enantioselective total syntheses of heliannuols B and D have been accomplished using chirality transfer through a Lewis acid-promoted Claisen rearrangement for the construction of the C7 tertiary stereogenic center and a relay ring-closing metathesis for assembling the dihydrobenzo[b]oxepine backbone of the natural products as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.070
• 作为产物：
  描述：

  三氟甲磺酸酐 、 Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以100%的产率得到(2S)-methyl 2-(trifluoromethylsulfonyloxy)-4-(tert-butyldiphenylsilyloxy)butanoate
  参考文献：
  名称：

  Concise total syntheses of heliannuols B and D

  摘要：

  Concise and efficient enantioselective total syntheses of heliannuols B and D have been accomplished using chirality transfer through a Lewis acid-promoted Claisen rearrangement for the construction of the C7 tertiary stereogenic center and a relay ring-closing metathesis for assembling the dihydrobenzo[b]oxepine backbone of the natural products as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.070

文献信息

• Concise total syntheses of heliannuols B and D
  作者：Yuki Manabe、Makoto Kanematsu、Hiromasa Yokoe、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tet.2013.11.070

  日期：2014.1

  Concise and efficient enantioselective total syntheses of heliannuols B and D have been accomplished using chirality transfer through a Lewis acid-promoted Claisen rearrangement for the construction of the C7 tertiary stereogenic center and a relay ring-closing metathesis for assembling the dihydrobenzo[b]oxepine backbone of the natural products as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.