((2S,3S)-3-Azido-tetrahydro-furan-2-yl)-methanol | 552859-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: ((2S,3S)-3-Azido-tetrahydro-furan-2-yl)-methanol
• 英文别名: [(2S,3S)-3-azidooxolan-2-yl]methanol
• CAS: 552859-23-1
• 化学式: C₅H₉N₃O₂
• 分子量: 143.145
• InChiKey: NNFFDSSCEMKCOP-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((2S,3S)-3-Azido-tetrahydro-furan-2-yl)-methanol 在 盐酸 、 palladium on activated charcoal 、 三丁基膦 、 甲酸铵 、 sodium cyanoborohydride 、 溶剂黄146 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.0h， 生成 2-{[(2R,3S)-3-(3,4-Dichloro-benzylamino)-tetrahydro-furan-2-ylmethyl]-amino}-1H-quinolin-4-one
  参考文献：
  名称：

  Conformational restriction of methionyl tRNA synthetase inhibitors leading to analogues with potent inhibition and excellent gram-Positive antibacterial activity

  摘要：

  Conformationally restricted analogues of the central linker unit of bacterial methionyl tRNA synthetase (MRS) inhibitors have been prepared. The (IS,2R)-cyclopentylmethyl moiety was identified as the preferred cyclic linker, with significant diastereo- and enantio selectivity of activity. Combination of this linker with an optimal substituted aryl right-hand side has resulted in a compound with exceptionally good antibacterial activity against staphylococci and enterococci, including antibiotic resistant strains. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00093-3
• 作为产物：
  描述：

  (2S,3S)-3-Azido-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 ((2S,3S)-3-Azido-tetrahydro-furan-2-yl)-methanol
  参考文献：
  名称：

  Conformational restriction of methionyl tRNA synthetase inhibitors leading to analogues with potent inhibition and excellent gram-Positive antibacterial activity

  摘要：

  Conformationally restricted analogues of the central linker unit of bacterial methionyl tRNA synthetase (MRS) inhibitors have been prepared. The (IS,2R)-cyclopentylmethyl moiety was identified as the preferred cyclic linker, with significant diastereo- and enantio selectivity of activity. Combination of this linker with an optimal substituted aryl right-hand side has resulted in a compound with exceptionally good antibacterial activity against staphylococci and enterococci, including antibiotic resistant strains. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00093-3