(E)-((1-isopropoxy-3-methylbut-1-en-1-yl)oxy)trimethylsilane | 1583259-22-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-((1-isopropoxy-3-methylbut-1-en-1-yl)oxy)trimethylsilane
• 英文别名: trimethyl-[(E)-3-methyl-1-propan-2-yloxybut-1-enoxy]silane
• CAS: 1583259-22-6
• 化学式: C₁₁H₂₄O₂Si
• 分子量: 216.396
• InChiKey: OOKCXCHROGHHNS-DHZHZOJOSA-N

物化性质

• 沸点：
  213.8±23.0 °C(predicted)
• 密度：
  0.856±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal 、 (E)-((1-isopropoxy-3-methylbut-1-en-1-yl)oxy)trimethylsilane 在 二异丙氧基二氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以94%的产率得到(2S,3S,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-isopropyl-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate
  参考文献：
  名称：

  A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir

  摘要：

  An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective alpha-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.

  DOI：

  10.1021/ja502205q
• 作为产物：
  描述：

  异戊酸 在 盐酸 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 15.0h， 生成 (E)-((1-isopropoxy-3-methylbut-1-en-1-yl)oxy)trimethylsilane
  参考文献：
  名称：

  A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir

  摘要：

  An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective alpha-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.

  DOI：

  10.1021/ja502205q