methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonylamino)-2-phenylethyl]-oxirane-2-carboxylate | 864165-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonylamino)-2-phenylethyl]-oxirane-2-carboxylate
• 英文别名: methyl (2R,3S)-3-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylethyl]oxirane-2-carboxylate
• CAS: 864165-75-3
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: OOFRFUVLUFTOLL-MELADBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonylamino)-2-phenylethyl]-oxirane-2-carboxylate 在 5%-palladium/activated carbon 、 水 、 氢气 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 20.0 ℃ 、1.01 MPa 条件下， 反应 73.0h， 生成 (3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-5-phenylpentanoic acid
  参考文献：
  名称：

  Stereodivergent approach to both syn- and anti-isomers of γ-amino-β-hydroxy acids: (3S,4S)- and (3R,4S)-AHPPA derivatives

  摘要：

  A stereodivergent approach employing an N-hydroxymethyl group has been utilized to produce both diastereomeric derivatives of (3S,4S)-AHPPA 3 and (312,4S)-AHPPA 4, via an intramolecular conjugate addition and an intramolecular epoxidation, respectively. The selectivity of the intramolecular conjugate addition was more than 10:1 while that of the intramolecular epoxidation was more than 1:20. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.09.021
• 作为产物：
  描述：

  methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonyl-N-hydroxymethylamino)-2-phenylethyl]-oxirane-2-carboxylate 在 甲醇 、 重铬酸吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonylamino)-2-phenylethyl]-oxirane-2-carboxylate
  参考文献：
  名称：

  Stereodivergent approach to both syn- and anti-isomers of γ-amino-β-hydroxy acids: (3S,4S)- and (3R,4S)-AHPPA derivatives

  摘要：

  A stereodivergent approach employing an N-hydroxymethyl group has been utilized to produce both diastereomeric derivatives of (3S,4S)-AHPPA 3 and (312,4S)-AHPPA 4, via an intramolecular conjugate addition and an intramolecular epoxidation, respectively. The selectivity of the intramolecular conjugate addition was more than 10:1 while that of the intramolecular epoxidation was more than 1:20. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.09.021