(4S,5S)-N-benzyloxycarbonyl-2,2,4-trimethyloxazolidin-5-carboxylic acid | 172097-59-5

• 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: (4S,5S)-N-benzyloxycarbonyl-2,2,4-trimethyloxazolidin-5-carboxylic acid
• 英文别名: (4S,5S)-2,2,4-trimethyl-3-phenylmethoxycarbonyl-1,3-oxazolidine-5-carboxylic acid
• CAS: 172097-59-5
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: XGAYSVMQRFNTFA-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (4S,5S)-N-benzyloxycarbonyl-2,2,4-trimethyloxazolidin-5-carboxylic acid 以 乙醚 为溶剂， 以71%的产率得到methyl (4S,5S)-N-benzyloxycarbonyl-2,2,4-trimethyloxazolidin-5-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of fully protected anti 3-amino-2-hydroxy butyrates

  摘要：

  An efficient enantioselective synthesis of fully protected anti 3-amino-2hydroxybutyrates has been developed. Starting from enantiomerically enriched anti N-diphenylmethyl-3-amino-1,2-butanediol, after a change in the nitrogen protecting group, the primary alcohol was protected by regioselective reduction of the corresponding p-methoxybenzylidene acetal. Formation of the oxazolidine and deprotection of the primary alcohol followed by oxidation afforded protected alpha-hydroxy-beta-amino acids in good yield. Since the source of asymmetry is a catalytic Sharpless epoxidation, both enantiomeric series are available and the methodology developed here is expected to be of broad applicability.

  DOI：

  10.1016/0957-4166(95)00309-d
• 作为产物：
  描述：

  (2S,3S)-3-benzyloxycarbonylamino-1,2-butanediol 在 重铬酸吡啶 、 水 、 二异丁基氢化铝 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 52.0h， 生成 (4S,5S)-N-benzyloxycarbonyl-2,2,4-trimethyloxazolidin-5-carboxylic acid
  参考文献：
  名称：

  Enantioselective synthesis of fully protected anti 3-amino-2-hydroxy butyrates

  摘要：

  An efficient enantioselective synthesis of fully protected anti 3-amino-2hydroxybutyrates has been developed. Starting from enantiomerically enriched anti N-diphenylmethyl-3-amino-1,2-butanediol, after a change in the nitrogen protecting group, the primary alcohol was protected by regioselective reduction of the corresponding p-methoxybenzylidene acetal. Formation of the oxazolidine and deprotection of the primary alcohol followed by oxidation afforded protected alpha-hydroxy-beta-amino acids in good yield. Since the source of asymmetry is a catalytic Sharpless epoxidation, both enantiomeric series are available and the methodology developed here is expected to be of broad applicability.

  DOI：

  10.1016/0957-4166(95)00309-d

文献信息

• Enantioselective synthesis of fully protected anti 3-amino-2-hydroxy butyrates
  作者：Mireia Pastó、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1016/0957-4166(95)00309-d

  日期：1995.9

  An efficient enantioselective synthesis of fully protected anti 3-amino-2hydroxybutyrates has been developed. Starting from enantiomerically enriched anti N-diphenylmethyl-3-amino-1,2-butanediol, after a change in the nitrogen protecting group, the primary alcohol was protected by regioselective reduction of the corresponding p-methoxybenzylidene acetal. Formation of the oxazolidine and deprotection of the primary alcohol followed by oxidation afforded protected alpha-hydroxy-beta-amino acids in good yield. Since the source of asymmetry is a catalytic Sharpless epoxidation, both enantiomeric series are available and the methodology developed here is expected to be of broad applicability.