(2R,4S)-2,4-bis[(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxy]pentanoic acid | 144762-94-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,4S)-2,4-bis[(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxy]pentanoic acid
• CAS: 144762-94-7
• 化学式: C₂₁H₃₆N₂O₈
• 分子量: 444.525
• InChiKey: SMHKBLQBTYYOTL-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,4S)-2,4-bis[(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxy]pentanoic acid 在 盐酸 作用下， 反应 16.0h， 以73%的产率得到syn-3-hydroxy-5-methyltetrahydrofuran-2-one
  参考文献：
  名称：

  Stereoselective generation of 1,3- and 1,4-dioxy-substituted carbanions by sparteine-assisted deprotonation of chiral precursors: Substrate or reagent control in the synthesis of α,γ- and α,δ-diols

  摘要：

  The deprotonation of a dicarbamate, derived from (S)-butane-1,3-diol, by sec-butyllithium takes an highly diastereoselective, but opposite, direction in the presence of (-)-sparteine and of tetramethylethylenediamine (TMEDA), respectively. The (S)-pentane-1,4-diol derivative shows the same stereochemical preference under both conditions.

  DOI：

  10.1016/s0040-4039(00)79084-8
• 作为产物：
  描述：

  二氧化碳 、 [(3S)-3-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxybutyl] 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 仲丁基锂 、 鹰爪豆碱 作用下， 生成 (2R,4S)-2,4-bis[(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxy]pentanoic acid
  参考文献：
  名称：

  Stereoselective generation of 1,3- and 1,4-dioxy-substituted carbanions by sparteine-assisted deprotonation of chiral precursors: Substrate or reagent control in the synthesis of α,γ- and α,δ-diols

  摘要：

  The deprotonation of a dicarbamate, derived from (S)-butane-1,3-diol, by sec-butyllithium takes an highly diastereoselective, but opposite, direction in the presence of (-)-sparteine and of tetramethylethylenediamine (TMEDA), respectively. The (S)-pentane-1,4-diol derivative shows the same stereochemical preference under both conditions.

  DOI：

  10.1016/s0040-4039(00)79084-8

文献信息

• JPH05286949A
  申请人：——

  公开号：JPH05286949A

  公开（公告）日：1993-11-02
• Stereoselective generation of 1,3- and 1,4-dioxy-substituted carbanions by sparteine-assisted deprotonation of chiral precursors: Substrate or reagent control in the synthesis of α,γ- and α,δ-diols
  作者：Hartmut Ahrens、Mario Paetow、Dieter Hoppe

  DOI：10.1016/s0040-4039(00)79084-8

  日期：1992.9

  The deprotonation of a dicarbamate, derived from (S)-butane-1,3-diol, by sec-butyllithium takes an highly diastereoselective, but opposite, direction in the presence of (-)-sparteine and of tetramethylethylenediamine (TMEDA), respectively. The (S)-pentane-1,4-diol derivative shows the same stereochemical preference under both conditions.