(2R,3R)-1,2-epoxy-3-azido-5-methylhexane | 142810-31-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2R,3R)-1,2-epoxy-3-azido-5-methylhexane
• 英文别名: (2S)-2-[(1R)-1-azido-3-methylbutyl]oxirane
• CAS: 142810-31-9
• 化学式: C₇H₁₃N₃O
• 分子量: 155.2
• InChiKey: ZTANSLBRNQTPRN-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1,2-epoxy-3-azido-5-methylhexane 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 双氧水 作用下， 以 甲醇 、 乙醇 、 水 、 叔丁醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 5.0h， 生成 (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：

  5-methylhex-1-en-3-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 迭氮酸 、 L-(+)-酒石酸二异丙酯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 反应 1.25h， 生成 (2R,3R)-1,2-epoxy-3-azido-5-methylhexane
  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.
• Inhibition of cathepsin D by tripeptides containing statine analogs
  作者：Michel Bessodes、Kostas Antonakis、Jean Herscovici、Marcel Garcia、Henri Rochefort、Françoise Capony、Yves Lelièvre、Daniel Scherman

  DOI：10.1016/s0006-2952(99)00103-3

  日期：1999.7

  Various analogs of statine, a remarkable amino acid component of the protease inhibitor pepstatine, were synthesized and evaluated as tripeptide derivatives for their activity against cathepsin D and HIV-1 protease. (C) 1999 Elsevier Science Inc.