(2S,5R,1'R)-2-tert-butyl-5-(1-hydroxy-1-trimethylsilanyl-ethyl)-5-methyl-1,3-dioxolan-4-one | 495389-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: (2S,5R,1'R)-2-tert-butyl-5-(1-hydroxy-1-trimethylsilanyl-ethyl)-5-methyl-1,3-dioxolan-4-one
• 英文别名: (2S,5S)-2-tert-butyl-5-[(1R)-1-hydroxy-1-trimethylsilylethyl]-5-methyl-1,3-dioxolan-4-one
• CAS: 495389-18-9
• 化学式: C₁₃H₂₆O₄Si
• 分子量: 274.433
• InChiKey: YLHAJGYPDWLOFM-KGYLQXTDSA-N

物化性质

• 沸点：
  352.5±22.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5R,1'R)-2-tert-butyl-5-(1-hydroxy-1-trimethylsilanyl-ethyl)-5-methyl-1,3-dioxolan-4-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以91%的产率得到methyl (2R,3R)-2,3-dihydroxy-2-methyl-3-trimethylsilanyl-butanoate
  参考文献：
  名称：

  Synthesis and desilylation of (2R,3S)-α-methyl-α-silyl-α,β-2,3-dihydroxycarboxylic methyl esters

  摘要：

  Addition reactions of the chiral lithium (2S)-enolates of the (2S,5S)-2-tert-butyl-5,-methyl-[1,3]dioxolan-4-one and (2S,5S)-2-tert-butyl-2,5-dimethyl-[1,3]dioxolan-4-one with linear aliphatic acylsilanes yield the corresponding (2S,5R,1'R)-1'-trimethylsilyl-dioxolanone alcohols. Sodium methoxide-induced removal of the acetal center at C-2 affords the corresponding methyl (2R,3R)-2,3-dihydroxy-2-methyl-3-trimethylsilyl alkanoates. The desilylation of these esters occurs with complete retention of configuration yielding the corresponding (2R,3S)-2,3-dihydroxy-2-methyl-alkanoic acids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00440-8
• 作为产物：
  描述：

  1-(trimethylsilyl)ethanone 、 (5S)-2-tert-butyl-2-methyl-1,3-dioxolan-4-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 生成 (2S,5R,1'R)-2-tert-butyl-5-(1-hydroxy-1-trimethylsilanyl-ethyl)-5-methyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  Synthesis and desilylation of (2R,3S)-α-methyl-α-silyl-α,β-2,3-dihydroxycarboxylic methyl esters

  摘要：

  Addition reactions of the chiral lithium (2S)-enolates of the (2S,5S)-2-tert-butyl-5,-methyl-[1,3]dioxolan-4-one and (2S,5S)-2-tert-butyl-2,5-dimethyl-[1,3]dioxolan-4-one with linear aliphatic acylsilanes yield the corresponding (2S,5R,1'R)-1'-trimethylsilyl-dioxolanone alcohols. Sodium methoxide-induced removal of the acetal center at C-2 affords the corresponding methyl (2R,3R)-2,3-dihydroxy-2-methyl-3-trimethylsilyl alkanoates. The desilylation of these esters occurs with complete retention of configuration yielding the corresponding (2R,3S)-2,3-dihydroxy-2-methyl-alkanoic acids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00440-8