(-)-(2S,6R)-methyl 6-(2-((triisopropylsilyl)oxy)ethyl)tetrahydro-2H-pyran-2-carboxylate | 1318231-17-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-(2S,6R)-methyl 6-(2-((triisopropylsilyl)oxy)ethyl)tetrahydro-2H-pyran-2-carboxylate
• CAS: 1318231-17-2
• 化学式: C₁₈H₃₆O₄Si
• 分子量: 344.567
• InChiKey: TVFNOTAHGCZXDO-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (-)-(2S,6R)-methyl 6-(2-((triisopropylsilyl)oxy)ethyl)tetrahydro-2H-pyran-2-carboxylate 、 溴甲苯 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 以74%的产率得到(-)-2-((2R,6S)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethanol
  参考文献：
  名称：

  Synthetic Versatility in C–H Oxidation: A Rapid Approach to Differentiated Diols and Pyrans from Simple Olefins

  摘要：

  Conventionally, C-H oxidation reactions are used to install functional groups. The use of C-H oxidation to transform simple starting materials into highly versatile intermediates, which enable rapid access to a range of complex target structures, is a new area with tremendous potential in synthesis. Herein we report a Pd(II)/sulfoxide-catalyzed allylic C-H oxidation to form anti-1,4-dioxan-2-ones from homoallylic oxygenates. These versatile building blocks are rapidly elaborated to differentiated syn-1,2-diols, stereo-defined amino-polyols, and syn-pyrans, structures ubiquitous in medicinally important complex molecules found in Nature. We also demonstrate that a C-H oxidation approach to the synthesis of these motifs is orthogonal and complementary to other state-of-the-art methods.

  DOI：

  10.1021/ja206013j
• 作为产物：
  描述：

  (5S)-5-(2-(triisopropylsilyloxy)ethyl)-6-vinyl-1,4-dioxan-2-one 在 三甲基氯硅烷 、 5%-palladium/activated carbon 、 氢气 、 potassium carbonate 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 (-)-(2R,6R)-methyl 6-(2-((triisopropylsilyl)oxy)ethyl)tetrahydro-2H-pyran-2-carboxylate 、 (-)-(2S,6R)-methyl 6-(2-((triisopropylsilyl)oxy)ethyl)tetrahydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Synthetic Versatility in C–H Oxidation: A Rapid Approach to Differentiated Diols and Pyrans from Simple Olefins

  摘要：

  Conventionally, C-H oxidation reactions are used to install functional groups. The use of C-H oxidation to transform simple starting materials into highly versatile intermediates, which enable rapid access to a range of complex target structures, is a new area with tremendous potential in synthesis. Herein we report a Pd(II)/sulfoxide-catalyzed allylic C-H oxidation to form anti-1,4-dioxan-2-ones from homoallylic oxygenates. These versatile building blocks are rapidly elaborated to differentiated syn-1,2-diols, stereo-defined amino-polyols, and syn-pyrans, structures ubiquitous in medicinally important complex molecules found in Nature. We also demonstrate that a C-H oxidation approach to the synthesis of these motifs is orthogonal and complementary to other state-of-the-art methods.

  DOI：

  10.1021/ja206013j