| 204767-24-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• CAS: 204767-24-8
• 化学式: C₁₃H₂₃NO₆
• 分子量: 294.289
• InChiKey: AWGYBVSFRIHNOB-WZDDVJCJSA-N

物化性质

• 沸点：
  443.965±40.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.138±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 、 sodium tetrahydroborate 、 Dowex 50W-X₈ 、 三正丁基氢锡 作用下， 生成 (2S,3S,4S)-[3,4,5,5,5-D5]leucine
  参考文献：
  名称：

  Stereoselective deuterium-labelling of diastereotopic methyl and methylene protons of L-leucine

  摘要：

  An asymmetric synthesis of regio-and stereoselectively deuterium-labelled L-leucine was examined using 4-hydoxy-L-poline as a chiral template. An enol triflate of 4-oxoproline prepared from 4-hydroxyproline was effectively methylated by a Gilman reagent to afford a 4-methyl-3,4-dehydroproline derivative. Then, a catalytic deuteration of the dehydroproline followed by RuO4-oxidation gave a deuterated 4-methylpyroglutamic acid derivative that could easily be converted to (2S,3S,4R)-leucine-3,4,5,5-d(5) via a base-promoted ring opening and a reductive deuteration of the terminal carboxyl moiety. This strategy wits also applied to the stereoselective synthesis of (2S,3S,4S)-[3,4,5,5,5-D-5]leucine. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00037-9
• 作为产物：
  描述：

  1-(tert-butyl) 2-ethyl (S)-4-oxopyrrolidine-1,2-dicarboxylate 在 platinum(IV) oxide lithium hydroxide 、 四氧化钌 、 sodium hexamethyldisilazane 、 氘 作用下， 以 四氢呋喃 、 氘代甲醇-d 为溶剂， 生成
  参考文献：
  名称：

  Stereoselective deuterium-labelling of diastereotopic methyl and methylene protons of L-leucine

  摘要：

  An asymmetric synthesis of regio-and stereoselectively deuterium-labelled L-leucine was examined using 4-hydoxy-L-poline as a chiral template. An enol triflate of 4-oxoproline prepared from 4-hydroxyproline was effectively methylated by a Gilman reagent to afford a 4-methyl-3,4-dehydroproline derivative. Then, a catalytic deuteration of the dehydroproline followed by RuO4-oxidation gave a deuterated 4-methylpyroglutamic acid derivative that could easily be converted to (2S,3S,4R)-leucine-3,4,5,5-d(5) via a base-promoted ring opening and a reductive deuteration of the terminal carboxyl moiety. This strategy wits also applied to the stereoselective synthesis of (2S,3S,4S)-[3,4,5,5,5-D-5]leucine. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00037-9