6,6'-dibromo-2,3,4,2',3',4'-hexa-O-benzoyl-6,6'-dideoxy-α,α-trehalose | 18933-86-3

• 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: 6,6'-dibromo-2,3,4,2',3',4'-hexa-O-benzoyl-6,6'-dideoxy-α,α-trehalose
• 英文别名: 6,6'-Dibrom-6,6'-dideoxy-α,α-trehalose-hexabenzoat；[(2S,3S,4S,5R,6R)-4,5-dibenzoyloxy-2-(bromomethyl)-6-[(2R,3R,4S,5S,6S)-3,4,5-tribenzoyloxy-6-(bromomethyl)oxan-2-yl]oxyoxan-3-yl] benzoate
• CAS: 18933-86-3
• 化学式: C₅₄H₄₄Br₂O₁₅
• 分子量: 1092.74
• InChiKey: KBWUSEOIEDXYKC-YBWLRKLZSA-N

物化性质

• 沸点：
  1024.1±65.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  71.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  185.49
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  6,6'-dibromo-2,3,4,2',3',4'-hexa-O-benzoyl-6,6'-dideoxy-α,α-trehalose 在 palladium on activated charcoal 盐酸 、 sodium azide 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 90.08h， 生成 2,3,4,2',3',4'-hexa-O-benzoyl6,6'-dideoxy-6,6'-bis[(phenylsulfonyl)amino]-α,α-trehalose
  参考文献：
  名称：

  Synthesis and biological evaluation of trehalose analogs as potential inhibitors of mycobacterial cell wall biosynthesis

  摘要：

  Analogs of trehalose are reported that were designed to interfere with mycolylation pathways in the mycobacterial cell wall. Several derivatives of 6,6'-dideoxytrehalose, including N,N'-dialkylamino and 6,6'-bis(sulfonamido) analogs, were prepared and evaluated for antimycobacterial activity against Mycobacterium tuberculosis H(37)Ra and a panel of clinical isolates of Mycobacterium avium, 6,6'-Diamitiotrehalose and its diazido precursor were both inactive, but significant activity apparently related to aliphatic chain length was found among the sulfonamides, N-alkylamines, and one of the amidines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00288-9
• 作为产物：
  描述：

  海藻糖 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 zinc(II) chloride 作用下， 以 四氯化碳 为溶剂， 反应 210.0h， 生成 6,6'-dibromo-2,3,4,2',3',4'-hexa-O-benzoyl-6,6'-dideoxy-α,α-trehalose
  参考文献：
  名称：

  Synthesis and biological evaluation of trehalose analogs as potential inhibitors of mycobacterial cell wall biosynthesis

  摘要：

  Analogs of trehalose are reported that were designed to interfere with mycolylation pathways in the mycobacterial cell wall. Several derivatives of 6,6'-dideoxytrehalose, including N,N'-dialkylamino and 6,6'-bis(sulfonamido) analogs, were prepared and evaluated for antimycobacterial activity against Mycobacterium tuberculosis H(37)Ra and a panel of clinical isolates of Mycobacterium avium, 6,6'-Diamitiotrehalose and its diazido precursor were both inactive, but significant activity apparently related to aliphatic chain length was found among the sulfonamides, N-alkylamines, and one of the amidines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00288-9