(2R,3S)-1,2-epoxy-3-hydroxy-5-methylhexane | 142839-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-1,2-epoxy-3-hydroxy-5-methylhexane
• 英文别名: (1S)-3-methyl-1-[(2R)-oxiran-2-yl]butan-1-ol
• CAS: 142839-56-3
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: MEIFSCYJGYRGFU-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-1,2-epoxy-3-hydroxy-5-methylhexane 在 Zn(N3)2-2 pyr 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 苯 为溶剂， 反应 2.83h， 生成 (2R,3S)-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
• 作为产物：
  描述：

  5-methylhex-1-en-3-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 作用下， 生成 (2R,3S)-1,2-epoxy-3-hydroxy-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

• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSÉS ORGANIQUES
  申请人：BARRY CLIFTON

  公开号：WO2011087995A2

  公开（公告）日：2011-07-21

  This invention provides compounds which are useful in the treatment of mycobacterial infections, pharmaceutical compositions containing the compounds, processes for their preparation, and uses of the compounds in various medicinal applications, such as the treatment or prevention of mycobacterial infections, such as those caused by Mycobacterium tuberculosis, Mycobacterium bovis, Mycobacterium leprae, Mycobacterium africanum, Mycobacterium avium, Mycobacterium microti, or any mycobacterium that causes multi-drug resistant (MDR) TB or extensively resistant (XDR) TB, or any other mycobacterial species known to cause disease in humans; or the treatment or prevention of parasitic diseases, such as those caused by a parasite of the genus Trypanosoma, e.g. Trypanosoma cruzi or Trypanosoma brucei or a parasite of the genus Leishmania which causes visceral leishmaniasis or kala-azar, e.g., Leishmania donovani.
• 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.