(4S)-4-[(2S)-2-hydroxy-3-nitropropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-4-[(2S)-2-hydroxy-3-nitropropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-[(2S)-2-hydroxy-3-nitropropyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• 化学式: C₁₃H₂₄N₂O₆
• 分子量: 304.343
• InChiKey: AGUAAHXWMWPLTE-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(2-羟基乙基)-2,2-二甲基噁唑啉-3-羧酸-(S)-叔丁酯 在 copper diacetate 、 草酰氯 、 2,2-bis[(3aS,8aR)-3a,8,8a-3H-indeno[3,2-d]oxazol-2yl]propane 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 121.5h， 生成 (4S)-4-[(2S)-2-hydroxy-3-nitropropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Highly Efficient Approach to Orthogonally Protected (2S,4R)- and (2S,4S)-4-Hydroxyornithine

  摘要：

  A concise stereoselective approach to both orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine, key constituents of the biphenomycin- and clavalanine-type antibiotics, respectively, has been developed. The approach is based on bis(oxazoline) copper(II)-complex-catalyzed diastereoselective Henry reactions of nitromethane with the homoserine-derived aldehyde 6. The synthesis of this versatile chiral building block has been markedly improved.

  DOI：

  10.1021/ol0503182

文献信息

• WO2006/94770
  申请人：——

  公开号：——

  公开（公告）日：——
• Highly Efficient Approach to Orthogonally Protected (2<i>S</i>,4<i>R</i>)- and (2<i>S</i>,4<i>S</i>)-4-Hydroxyornithine
  作者：Franz F. Paintner、Lars Allmendinger、Gerd Bauschke、Patricia Klemann

  DOI：10.1021/ol0503182

  日期：2005.3.1

  A concise stereoselective approach to both orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine, key constituents of the biphenomycin- and clavalanine-type antibiotics, respectively, has been developed. The approach is based on bis(oxazoline) copper(II)-complex-catalyzed diastereoselective Henry reactions of nitromethane with the homoserine-derived aldehyde 6. The synthesis of this versatile chiral building block has been markedly improved.