(3R,4R)-4-azido-3-hydroxy-6-methylheptanamide | 142810-38-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,4R)-4-azido-3-hydroxy-6-methylheptanamide
• CAS: 142810-38-6
• 化学式: C₈H₁₆N₄O₂
• 分子量: 200.241
• InChiKey: SLWSCNARNHNCCQ-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  77.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-azido-3-hydroxy-6-methylheptanamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以92%的产率得到(3R,4R)-4-amino-3-hydroxy-6-methylheptanamide
  参考文献：
  名称：

  A new, versatile and stereospecific route to unusual amino acids: the enantiospecific total synthesis of statine amide and its three stereoisomers

  摘要：

  Total syntheses of statine amide [(3S,4S)-4-amino-3-hydroxy-6-methylheptanamide] and its three stereoisomers are described in order to illustrate the versatility of a new route to beta-hydroxy-gamma-amino acids. The enantioselective Sharpless epoxidation of a racemic allylic alcohol is used to generate chiral intermediates. The allylic alcohol, 3-hydroxy-5-methyl-1-hexene, can be prepared in at least two different ways from readily available materials. The methodology that is described should prove applicable to the synthesis of other analogues of statine.

  DOI：

  10.1021/jo00042a026
• 作为产物：
  描述：

  (3R,4R)-4-azido-3-hydroxy-6-methylheptanenitrile 在 sodium hydroxide 、 双氧水 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.0h， 以95%的产率得到(3R,4R)-4-azido-3-hydroxy-6-methylheptanamide
  参考文献：
  名称：

  A new, versatile and stereospecific route to unusual amino acids: the enantiospecific total synthesis of statine amide and its three stereoisomers

  摘要：

  Total syntheses of statine amide [(3S,4S)-4-amino-3-hydroxy-6-methylheptanamide] and its three stereoisomers are described in order to illustrate the versatility of a new route to beta-hydroxy-gamma-amino acids. The enantioselective Sharpless epoxidation of a racemic allylic alcohol is used to generate chiral intermediates. The allylic alcohol, 3-hydroxy-5-methyl-1-hexene, can be prepared in at least two different ways from readily available materials. The methodology that is described should prove applicable to the synthesis of other analogues of statine.

  DOI：

  10.1021/jo00042a026

文献信息

• A new, versatile and stereospecific route to unusual amino acids: the enantiospecific total synthesis of statine amide and its three stereoisomers
  作者：M. Bessodes、M. Saiah、K. Antonakis

  DOI：10.1021/jo00042a026

  日期：1992.7

  Total syntheses of statine amide [(3S,4S)-4-amino-3-hydroxy-6-methylheptanamide] and its three stereoisomers are described in order to illustrate the versatility of a new route to beta-hydroxy-gamma-amino acids. The enantioselective Sharpless epoxidation of a racemic allylic alcohol is used to generate chiral intermediates. The allylic alcohol, 3-hydroxy-5-methyl-1-hexene, can be prepared in at least two different ways from readily available materials. The methodology that is described should prove applicable to the synthesis of other analogues of statine.