methyl (S)-4-(tert-butyldimethylsilyloxy)-3-methylbutanoate | 862387-14-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (S)-4-(tert-butyldimethylsilyloxy)-3-methylbutanoate
• 英文别名: methyl (3S)-4-[tert-butyl(dimethyl)silyl]oxy-3-methylbutanoate
• CAS: 862387-14-2
• 化学式: C₁₂H₂₆O₃Si
• 分子量: 246.422
• InChiKey: SXPZQMQBQXOVDD-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (S)-4-(tert-butyldimethylsilyloxy)-3-methylbutanoate 在 正丁基锂 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.34h， 生成 (S,E)-7-(tert-butyldimethylsilyloxy)-6-methylhept-2-en-4-one
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-Dihydroxanthatin by the Stereoselective Oshima−Utimoto Reaction

  摘要：

  The catalytic stereoselective Oshima-Utimoto reaction is useful for the construction of five-membered oxacycles from simple starting materials and was employed for the preparation of the lactone group in the asymmetric synthesis of (-)-11 alpha,13-dihydroxanthatin. Completion of the synthesis is facilitated by ring-closing enyne metathesis and alkene cross metathesis reactions.

  DOI：

  10.1021/ol051276k
• 作为产物：
  描述：

  (3S)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyronitrile 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 二异丁基氢化铝 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 2.5h， 生成 methyl (S)-4-(tert-butyldimethylsilyloxy)-3-methylbutanoate
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-Dihydroxanthatin by the Stereoselective Oshima−Utimoto Reaction

  摘要：

  The catalytic stereoselective Oshima-Utimoto reaction is useful for the construction of five-membered oxacycles from simple starting materials and was employed for the preparation of the lactone group in the asymmetric synthesis of (-)-11 alpha,13-dihydroxanthatin. Completion of the synthesis is facilitated by ring-closing enyne metathesis and alkene cross metathesis reactions.

  DOI：

  10.1021/ol051276k

文献信息

• Total Syntheses of Amphidinolide H and G
  作者：Alois Fürstner、Laure C. Bouchez、Jacques-Alexis Funel、Vilnis Liepins、François-Hugues Porée、Ryan Gilmour、Florent Beaufils、Daniel Laurich、Minoru Tamiya

  DOI：10.1002/anie.200704024

  日期：2007.12.10
• Asymmetric Synthesis of (−)-Dihydroxanthatin by the Stereoselective Oshima−Utimoto Reaction
  作者：Michael A. Evans、James P. Morken

  DOI：10.1021/ol051276k

  日期：2005.7.1

  The catalytic stereoselective Oshima-Utimoto reaction is useful for the construction of five-membered oxacycles from simple starting materials and was employed for the preparation of the lactone group in the asymmetric synthesis of (-)-11 alpha,13-dihydroxanthatin. Completion of the synthesis is facilitated by ring-closing enyne metathesis and alkene cross metathesis reactions.