tert-Butyl-((2S,5R,6S)-5-methoxy-6-pent-4-enyl-tetrahydro-pyran-2-ylmethoxy)-diphenyl-silane | 203172-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-((2S,5R,6S)-5-methoxy-6-pent-4-enyl-tetrahydro-pyran-2-ylmethoxy)-diphenyl-silane
• 英文别名: tert-butyl-[[(2S,5R,6S)-5-methoxy-6-pent-4-enyloxan-2-yl]methoxy]-diphenylsilane
• CAS: 203172-24-1
• 化学式: C₂₈H₄₀O₃Si
• 分子量: 452.709
• InChiKey: VUNDOEAWCXURBP-RNJDCESWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-Butyl-((2S,5R,6S)-5-methoxy-6-pent-4-enyl-tetrahydro-pyran-2-ylmethoxy)-diphenyl-silane 在 sodium tetrahydroborate 、 碘苯二乙酸 、 四丁基氟化铵 、 碘 、 臭氧 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 环己烷 为溶剂， 反应 32.67h， 生成 (2R,5R,6S)-2-But-3-enyl-5-methoxy-1,7-dioxa-spiro[5.5]undecane
  参考文献：
  名称：

  Syntheses of Chiral Dispiroacetals from Carbohydrates

  摘要：

  The syntheses of trioxadispiroacetals from carbohydrates are described. (5R,7S,13R)-13-Methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane (23) and (5S,7S,13R)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane (24) were prepared starting from D-galactose. The construction of the lateral tetrahydrofuran and tetrahydropyran rings was realized by homologation at C-1 and C-6 by appropriate tethers possessing a terminal primary alcohol. The cyclization of these alcohols at C-1 and C-5, respectively, was performed with (diacetoxyiodo)benzene and iodine in order to generate the alkoxy radicals which undergo an intramolecular hydrogen abstraction reaction. The diastereoisomers (5R,7S,13S)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane (37) and (5S,7S,13S)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane (38) were prepared starting from tri-O-acetyl-D-glucal using a suitable methodology in which homologation and intramolecular hydrogen abstraction were again the key steps. We believe that this protocol could be easily extended to other tricyclic dispiroacetal ring systems.

  DOI：

  10.1021/jo972023a
• 作为产物：
  描述：

  (2S,3R,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol 在 sodium hydroxide 、 三氯化硼-甲硫醚 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 tert-Butyl-((2S,5R,6S)-5-methoxy-6-pent-4-enyl-tetrahydro-pyran-2-ylmethoxy)-diphenyl-silane
  参考文献：
  名称：

  通过分子内氢提取从碳水化合物合成双螺缩醛

  摘要：

  描述了由d-吡喃半乳糖合成1,6,8-三恶二螺[4.1.5.3]十五烷15和16。关键步骤是由烷氧基促进的两个分子内氢提取反应。

  DOI：

  10.1016/0040-4039(96)01265-8

文献信息

• Synthesis of dispiroacetals from carbohydrates by intramolecular hydrogen abstractions
  作者：Rosa L. Dorta、Angeles Martín、JoséA. Salazar、Ernesto Suárez、Thierry Prangé

  DOI：10.1016/0040-4039(96)01265-8

  日期：1996.8

  The synthesis of 1,6,8-trioxadispiro[4.1.5.3]pentadecanes 15 and 16 from d-galactopyranose is described. The key steps are two intramolecular hydrogen abstraction reactions promoted by alkoxy radicals.

  描述了由d-吡喃半乳糖合成1,6,8-三恶二螺[4.1.5.3]十五烷15和16。关键步骤是由烷氧基促进的两个分子内氢提取反应。
• Syntheses of Chiral Dispiroacetals from Carbohydrates
  作者：Rosa L. Dorta、Angeles Martín、José A. Salazar、Ernesto Suárez、Thierry Prangé

  DOI：10.1021/jo972023a

  日期：1998.4.1

  The syntheses of trioxadispiroacetals from carbohydrates are described. (5R,7S,13R)-13-Methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane (23) and (5S,7S,13R)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane (24) were prepared starting from D-galactose. The construction of the lateral tetrahydrofuran and tetrahydropyran rings was realized by homologation at C-1 and C-6 by appropriate tethers possessing a terminal primary alcohol. The cyclization of these alcohols at C-1 and C-5, respectively, was performed with (diacetoxyiodo)benzene and iodine in order to generate the alkoxy radicals which undergo an intramolecular hydrogen abstraction reaction. The diastereoisomers (5R,7S,13S)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane (37) and (5S,7S,13S)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane (38) were prepared starting from tri-O-acetyl-D-glucal using a suitable methodology in which homologation and intramolecular hydrogen abstraction were again the key steps. We believe that this protocol could be easily extended to other tricyclic dispiroacetal ring systems.