(2R,3R,4R,5S,6S)-3-acetamido-6-(((dimethylcarbamothioyl)thio)methyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate | 1201794-22-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3R,4R,5S,6S)-3-acetamido-6-(((dimethylcarbamothioyl)thio)methyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate
• CAS: 1201794-22-0
• 化学式: C₁₇H₂₆N₂O₈S₂
• 分子量: 450.534
• InChiKey: CRYPLZASJWFUEQ-QCODTGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.22
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  120.47
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S,6S)-3-acetamido-6-(((dimethylcarbamothioyl)thio)methyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate 在 盐酸 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 生成 (2S,3S,4R,5R,6R)-5-acetamido-6-chloro-2-(((dimethylcarbamothioyl)thio)methyl)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  Synthesis of new sugar derivatives and evaluation of their antibacterial activities against Mycobacterium tuberculosis

  摘要：

  A series of sugar derivatives (1-13) were synthesized and evaluated for antibacterial activity against Mycobacterium tuberculosis (MTB), especially multi-drug resistant (MDR) MTB, and the structure-activity relationships of these compounds were studied. The results showed that the compound OCT313 (2-acetamido-2deoxy-beta-D-glucopyranosyl N,N-dimethyldithiocarbamate) (4) exhibited significant in vitro bactericidal activity, and that the dithiocarbamate group at C-1 position of the glucopyranoside ring was requisite for the antibacterial activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.095
• 作为产物：
  描述：

  methyl (2E,6E,10E,14E)-geranylfarnesoate 、 sodium dimethyldithiocarbamate 以 丙酮 为溶剂， 反应 1.0h， 以92.3%的产率得到(2R,3R,4R,5S,6S)-3-acetamido-6-(((dimethylcarbamothioyl)thio)methyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate
  参考文献：
  名称：

  Synthesis of new sugar derivatives and evaluation of their antibacterial activities against Mycobacterium tuberculosis

  摘要：

  A series of sugar derivatives (1-13) were synthesized and evaluated for antibacterial activity against Mycobacterium tuberculosis (MTB), especially multi-drug resistant (MDR) MTB, and the structure-activity relationships of these compounds were studied. The results showed that the compound OCT313 (2-acetamido-2deoxy-beta-D-glucopyranosyl N,N-dimethyldithiocarbamate) (4) exhibited significant in vitro bactericidal activity, and that the dithiocarbamate group at C-1 position of the glucopyranoside ring was requisite for the antibacterial activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.095