benzyl (2R)-2-[(2R,3R,4S,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-3-methoxy-6-[(2S)-1-methoxypropan-2-yl]-5-methyloxan-2-yl]propanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (2R)-2-[(2R,3R,4S,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-3-methoxy-6-[(2S)-1-methoxypropan-2-yl]-5-methyloxan-2-yl]propanoate
• 化学式: C₂₇H₄₆O₇Si
• 分子量: 510.744
• InChiKey: VJQFYRYNGIAVIQ-BQKDUZIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (2R)-2-[(2R,3R,4S,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-3-methoxy-6-[(2S)-1-methoxypropan-2-yl]-5-methyloxan-2-yl]propanoate 在 吡啶 、 氢氟酸 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以28%的产率得到(2'R,3'R,4'S,5'R,6'S)-2(R)-<2',4'-Dihydroxy-3'-methoxy-6'-(1''-methoxy-2''(S)-methylethyl)-5'-methyltetrahydropyran-2'-yl>propionic acid benzyl 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：

  丙酸苄酯 、 (3R,4S,5R,6S)-4-<(tert-Butyldimethylsilyl)oxy>-3-methoxy-6-(1'-methoxy-2'(S)-methylethyl)-5-methyltetrahydropyran-2-one 在 2,2,6,6-tetramethylpiperidinyl-lithium 、 silica gel 作用下， 生成 benzyl (2S)-2-[(2R,3R,4S,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-3-methoxy-6-[(2S)-1-methoxypropan-2-yl]-5-methyloxan-2-yl]propanoate 、 benzyl (2R)-2-[(2R,3R,4S,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-3-methoxy-6-[(2S)-1-methoxypropan-2-yl]-5-methyloxan-2-yl]propanoate 、 benzyl (2S)-2-[(2S,3R,4S,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-3-methoxy-6-[(2S)-1-methoxypropan-2-yl]-5-methyloxan-2-yl]propanoate 、 benzyl (2R)-2-[(2S,3R,4S,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-3-methoxy-6-[(2S)-1-methoxypropan-2-yl]-5-methyloxan-2-yl]propanoate
  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.