(4S)-[(2S)-3-benzyloxycarbonylamino-2-triisopropylsilanyloxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester | 850996-94-0

• 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)-[(2S)-3-benzyloxycarbonylamino-2-triisopropylsilanyloxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: (4S)-4-[(2S)-3-benzyloxycarbonylamino-2-triisopropylsilanyloxy-propyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester；tert-butyl (4S)-2,2-dimethyl-4-[(2S)-3-(phenylmethoxycarbonylamino)-2-tri(propan-2-yl)silyloxypropyl]-1,3-oxazolidine-3-carboxylate
• CAS: 850996-94-0
• 化学式: C₃₀H₅₂N₂O₆Si
• 分子量: 564.838
• InChiKey: UGBVZUSWTDEMRF-UIOOFZCWSA-N

物化性质

• 沸点：
  599.6±50.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.24
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-[(2S)-3-benzyloxycarbonylamino-2-triisopropylsilanyloxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以76%的产率得到(2S,4S)-1-hydroxy-4-triisopropylsilanyloxy-5-benzyloxycarbonylaminopent-2-ylaminocarboxylic 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
• 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 232.0h， 生成 (4S)-[(2S)-3-benzyloxycarbonylamino-2-triisopropylsilanyloxypropyl]-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.