2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalopyranuronic acid | 827025-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalopyranuronic acid
• CAS: 827025-76-3
• 化学式: C₅₄H₅₄O₁₃
• 分子量: 911.015
• InChiKey: MXKUHYNFLYGPRO-ARHVPXBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  67.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  157.67
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalopyranuronic acid 在 草酰氯 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (E)-3-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((E)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid methyl ester
  参考文献：
  名称：

  Synthesis of trehalose-based compounds and their inhibitory activities against Mycobacterium smegmatis

  摘要：

  The synthesis of a library of trehalose-based compounds has been accomplished, and their activities against mycobacterium smegmatis have been determined. A preliminary structure-activity relationship (SAR) is reported. Despite not having a potent lead, one of the trehalose derivatives displays strong activity when applied with isoniazid (INH), which is known to have low sterilizing activity. The bacteriocidal nature of our compounds against Mycobacterium may be significant for the development of new therapies against tuberculosis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.033
• 作为产物：
  描述：

  (2S,2'S,3S,3'S,4S,4'S,5R,5'R,6R,6'R)-6,6'-oxybis(3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-carbaldehyde) 在 sodium chlorite 、 disodium hydrogenphosphate 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以79%的产率得到2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalopyranuronic acid
  参考文献：
  名称：

  Synthesis of trehalose-based compounds and their inhibitory activities against Mycobacterium smegmatis

  摘要：

  The synthesis of a library of trehalose-based compounds has been accomplished, and their activities against mycobacterium smegmatis have been determined. A preliminary structure-activity relationship (SAR) is reported. Despite not having a potent lead, one of the trehalose derivatives displays strong activity when applied with isoniazid (INH), which is known to have low sterilizing activity. The bacteriocidal nature of our compounds against Mycobacterium may be significant for the development of new therapies against tuberculosis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.033