(2R,4S)-3-((R)-cyclopentyl(1-methyl-1H-imidazol-2-yl)methyl)-4-isopropyl-2-methoxyoxazolidine | 1373441-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2R,4S)-3-((R)-cyclopentyl(1-methyl-1H-imidazol-2-yl)methyl)-4-isopropyl-2-methoxyoxazolidine
• 英文别名: (2R,4S)-3-[(R)-Cyclopentyl(1-methyl-1H-imidazol-2-yl)methyl]-4-(iso-propyl)-2-methoxyoxazolidine；(2R,4S)-3-[(R)-cyclopentyl-(1-methylimidazol-2-yl)methyl]-2-methoxy-4-propan-2-yl-1,3-oxazolidine
• CAS: 1373441-02-1
• 化学式: C₁₇H₂₉N₃O₂
• 分子量: 307.436
• InChiKey: PTUMLLQHIGZMNO-BFYDXBDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  39.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  环戊基甲醛 在 正丁基锂 、 magnesium sulfate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 苯 为溶剂， 反应 3.5h， 生成 (2R,4S)-3-((R)-cyclopentyl(1-methyl-1H-imidazol-2-yl)methyl)-4-isopropyl-2-methoxyoxazolidine
  参考文献：
  名称：

  Site-Selective Catalysis: Toward a Regiodivergent Resolution of 1,2-Diols

  摘要：

  This paper demonstrates that the secondary hydroxyl can be functionalized in preference to the primary hydroxyl of a 1,2-diol. The site selectivity is achieved by using an enantioselective organic catalyst that is able to bond to the diol reversibly and covalently. The reaction has been parlayed into a divergent kinetic resolution on a racemic mixture, providing access to highly enantioenriched secondary-protected 1,2-diols in a single synthetic step.

  DOI：

  10.1021/ja3027086
• 作为试剂：
  描述：

  6-N-benzoyl-5'-O-(4,4'-dimethoxytrityl)adenosine 、 叔丁基二甲基氯硅烷 在 (2R,4S)-3-((R)-cyclopentyl(1-methyl-1H-imidazol-2-yl)methyl)-4-isopropyl-2-methoxyoxazolidine 、 N,N-二异丙基乙胺盐酸盐 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以82%的产率得到5'-O-（4,4'-二甲氧基三苯甲基）-2'-O-叔丁基二甲基硅基-N6-苯甲酰基腺苷
  参考文献：
  名称：

  Practical Silyl Protection of Ribonucleosides

  摘要：

  Herein we report the site-selective silylation of the ribonucelosides. The method enables a simple and efficient procedure for accessing suitably protected monomers for automated RNA synthesis. Switching to the opposite enantiomer of the catalyst allows for the selective silylation of the 3'-hydroxyl, which could be used in the synthesis of unnatural RNA or for the analoging of ribonucelosides. Lastly, the procedure was extended to ribavirin a potent antiviral therapeutic.

  DOI：

  10.1021/ol402023c

文献信息

• Site-Selective Catalysis: Toward a Regiodivergent Resolution of 1,2-Diols
  作者：Amanda D. Worthy、Xixi Sun、Kian L. Tan

  DOI：10.1021/ja3027086

  日期：2012.5.2

  This paper demonstrates that the secondary hydroxyl can be functionalized in preference to the primary hydroxyl of a 1,2-diol. The site selectivity is achieved by using an enantioselective organic catalyst that is able to bond to the diol reversibly and covalently. The reaction has been parlayed into a divergent kinetic resolution on a racemic mixture, providing access to highly enantioenriched secondary-protected 1,2-diols in a single synthetic step.