tert-butyl-[[(1S,4S,5R)-2,4-dimethyl-8-oxabicyclo[3.2.1]octa-2,6-dien-3-yl]oxy]-dimethylsilane | 401911-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: tert-butyl-[[(1S,4S,5R)-2,4-dimethyl-8-oxabicyclo[3.2.1]octa-2,6-dien-3-yl]oxy]-dimethylsilane
• CAS: 401911-77-1
• 化学式: C₁₅H₂₆O₂Si
• 分子量: 266.456
• InChiKey: DBLHCFYHPXWZIW-UHTWSYAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl-[[(1S,4S,5R)-2,4-dimethyl-8-oxabicyclo[3.2.1]octa-2,6-dien-3-yl]oxy]-dimethylsilane 在 2,6-二甲基吡啶 、 18-冠醚-6 、 四丁基氟化铵 、 lithium perchlorate 、 四丁基碘化铵 、 potassium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 (3R,3aR,4R,5R,6R,7R,8aR)-5-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-3,4,6-trimethyl-octahydro-cyclohepta[b]furan-2-one
  参考文献：
  名称：

  Oxabicyclo[3.2.1]octenes in Organic SynthesisDirect Ring Opening of Oxabicyclo[3.2.1] Systems Employing Silyl Ketene Acetals in Concentrated Solutions of Lithium Perchlorate−Diethyl Ether:  Application to the Synthesis of the C(19)−C(27) Fragment of Rifamycin S

  摘要：

  [GRAPHICS]The direct opening at the bridgehead of oxabicyclo[3.2.1]octenes employing silyl ketene acetals in 4.0-5.0 M lithium perchlorate in diethyl ether has been realized, which gives rise to highly functionalized cycloheptadienes that can be further manipulated for use in natural product synthesis. The bridgehead opening reaction has been employed in the construction of the C(19)-C(27) fragment of Rifamycin S.

  DOI：

  10.1021/ol0003836
• 作为产物：
  描述：

  无 、 叔丁基二甲基氯硅烷 在 lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 24.0h， 生成 tert-butyl-[[(1S,4S,5R)-2,4-dimethyl-8-oxabicyclo[3.2.1]octa-2,6-dien-3-yl]oxy]-dimethylsilane 、
  参考文献：
  名称：

  Oxabicyclo[3.2.1]octenes in Organic Synthesis:  Direct Ring Opening of Oxabicyclo[3.2.1] Ring Systems with Diisobutylaluminum Hydride and a Silyl Ketene AcetalSynthesis of the Chiral C(19)−C(26) and C(27)−C(32) Fragments of Scytophycin C

  摘要：

  GRAPHICSAn efficient strategy for transforming meso-oxabicyclo[3.2.1]octenone 1 into optically active intermediates for macrolide synthesis has been developed. The direct bridgehead opening of optically active oxabicyclo[3.2.1]octene derivative 2 with hydride or a silyl ketene acetal utilizing the highly polar medium lithium perchlorate in diethyl ether resulted in highly functionalized cycloheptenones, which were transformed into the C(19)-C(26) and C(27)-C(32) fragments of Scytophycin C.

  DOI：

  10.1021/ol010253c

文献信息

• Oxabicyclo[3.2.1]octenes in Organic Synthesis:  Direct Ring Opening of Oxabicyclo[3.2.1] Ring Systems with Diisobutylaluminum Hydride and a Silyl Ketene AcetalSynthesis of the Chiral C(19)−C(26) and C(27)−C(32) Fragments of Scytophycin C
  作者：Kevin W. Hunt、Paul A. Grieco

  DOI：10.1021/ol010253c

  日期：2002.1.1

  GRAPHICSAn efficient strategy for transforming meso-oxabicyclo[3.2.1]octenone 1 into optically active intermediates for macrolide synthesis has been developed. The direct bridgehead opening of optically active oxabicyclo[3.2.1]octene derivative 2 with hydride or a silyl ketene acetal utilizing the highly polar medium lithium perchlorate in diethyl ether resulted in highly functionalized cycloheptenones, which were transformed into the C(19)-C(26) and C(27)-C(32) fragments of Scytophycin C.
• Oxabicyclo[3.2.1]octenes in Organic SynthesisDirect Ring Opening of Oxabicyclo[3.2.1] Systems Employing Silyl Ketene Acetals in Concentrated Solutions of Lithium Perchlorate−Diethyl Ether:  Application to the Synthesis of the C(19)−C(27) Fragment of Rifamycin S
  作者：Kevin W. Hunt、Paul A. Grieco

  DOI：10.1021/ol0003836

  日期：2001.2.1

  [GRAPHICS]The direct opening at the bridgehead of oxabicyclo[3.2.1]octenes employing silyl ketene acetals in 4.0-5.0 M lithium perchlorate in diethyl ether has been realized, which gives rise to highly functionalized cycloheptadienes that can be further manipulated for use in natural product synthesis. The bridgehead opening reaction has been employed in the construction of the C(19)-C(27) fragment of Rifamycin S.