(3R,4S,5R,6S)-4-<(tert-Butyldimethylsilyl)oxy>-3-methoxy-6-(1'-methoxy-2'(S)-methylethyl)-5-methyltetrahydropyran-2-one | 162018-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,4S,5R,6S)-4-<(tert-Butyldimethylsilyl)oxy>-3-methoxy-6-(1'-methoxy-2'(S)-methylethyl)-5-methyltetrahydropyran-2-one
• 英文别名: (3R,4S,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-6-[(2S)-1-methoxypropan-2-yl]-5-methyloxan-2-one
• CAS: 162018-30-6
• 化学式: C₁₇H₃₄O₅Si
• 分子量: 346.539
• InChiKey: XHWZNEXLJNXVCX-AIEDFZFUSA-N

物化性质

• 沸点：
  389.5±42.0 °C(predicted)
• 密度：
  0.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙酸叔丁酯 、 (3R,4S,5R,6S)-4-<(tert-Butyldimethylsilyl)oxy>-3-methoxy-6-(1'-methoxy-2'(S)-methylethyl)-5-methyltetrahydropyran-2-one 在 正丁基锂 、 silica gel 、 二异丙胺 作用下， 生成 (3'R,4'S,5'R,6'S)-2-<4'-<(tert-Butyldimethylsilyl)oxy>-2'-hydroxy-3'-methoxy-6'-(1''-methoxy-2''(S)-methylethyl)-5'-methyltetrahydropyran-2'-yl>propionic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Southern-Part Models of Soraphen A

  摘要：

  A number of model compounds corresponding to substructures of the fungicidal macrolide soraphen A were prepared from the lactone 3. This lactone was obtained degradatively from soraphen A using the mild Japp-Klingemann variant of the retro-aldol reaction and ozonolysis of the double bond. Addition of ester enolates,ta the lactone 3 led to the isolation of unstable hemiacetals which were converted to their anomerically stabilized tautomers on chromatography or prolonged standing in solution. Because of the unusual stability of the initially formed hemiacetals it was possible to define the structures of the transition states of the addition of enolates to a lactone in unprecedented detail.

  DOI：

  10.1021/jo00109a028
• 作为产物：
  描述：

  (3R,4S,5R,6S)-4-<(tert-Butyldimethylsilyl)oxy>-6-(1'-hydroxy-2'(S)-methylethyl)-3-methoxy-5-methyltetrahydropyran-2-one 、 三氟甲烷磺酸甲酯 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到(3R,4S,5R,6S)-4-<(tert-Butyldimethylsilyl)oxy>-3-methoxy-6-(1'-methoxy-2'(S)-methylethyl)-5-methyltetrahydropyran-2-one
  参考文献：
  名称：

  Synthesis of Southern-Part Models of Soraphen A

  摘要：

  A number of model compounds corresponding to substructures of the fungicidal macrolide soraphen A were prepared from the lactone 3. This lactone was obtained degradatively from soraphen A using the mild Japp-Klingemann variant of the retro-aldol reaction and ozonolysis of the double bond. Addition of ester enolates,ta the lactone 3 led to the isolation of unstable hemiacetals which were converted to their anomerically stabilized tautomers on chromatography or prolonged standing in solution. Because of the unusual stability of the initially formed hemiacetals it was possible to define the structures of the transition states of the addition of enolates to a lactone in unprecedented detail.

  DOI：

  10.1021/jo00109a028

文献信息

• Synthesis of Southern-Part Models of Soraphen A
  作者：Bernard Loubinoux、Jean-Luc Sinnes、Anthony C. O'Sullivan、Tammo Winkler

  DOI：10.1021/jo00109a028

  日期：1995.2

  A number of model compounds corresponding to substructures of the fungicidal macrolide soraphen A were prepared from the lactone 3. This lactone was obtained degradatively from soraphen A using the mild Japp-Klingemann variant of the retro-aldol reaction and ozonolysis of the double bond. Addition of ester enolates,ta the lactone 3 led to the isolation of unstable hemiacetals which were converted to their anomerically stabilized tautomers on chromatography or prolonged standing in solution. Because of the unusual stability of the initially formed hemiacetals it was possible to define the structures of the transition states of the addition of enolates to a lactone in unprecedented detail.