6,6'-diazido-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose | 76790-47-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6'-diazido-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose
• 英文别名: 6,6'-diazido-2,2',3,3',4,4'-hexa-O-benzyl-6,6'-dideoxy-α-D-trehalose
• CAS: 76790-47-1
• 化学式: C₅₄H₅₆N₆O₉
• 分子量: 933.073
• InChiKey: WWLUTWNLKGVRPJ-IPCGEZBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.59
• 重原子数：
  69.0
• 可旋转键数：
  24.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  180.59
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  6,6'-diazido-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose 在 sodium hydroxide 、 三甲基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以76%的产率得到6,6'-diamino-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose
  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：

  2,3,4,2',3',4'-hexa-O-benzyl-6,6'-di-O-(methylsulfonyl)-α,α-trehalose 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以93%的产率得到6,6'-diazido-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose
  参考文献：
  名称：

  6,6′-Diamino-2,3,4,2′,3′,4′-hexa-O-benzyl 6,6′-dideoxy-α,α-trehalose

  摘要：

  DOI：

  10.1016/s0008-6215(00)85200-3

文献信息

• Sonochemistry:  A Powerful Way of Enhancing the Efficiency of Carbohydrate Synthesis
  作者：Shenglou Deng、Umesh Gangadharmath、Cheng-Wei Tom Chang

  DOI：10.1021/jo060374w

  日期：2006.7.1

  [GRAPHICS]Using sonication as a means of facilitating organic reactions in carbohydrate chemistry was explored under the conditions used for traditional organic synthesis. An array of representative reactions, including hydroxy group manipulation ( acylation, protection/deprotection, acyl group migration), thioglycoside synthesis, azidoglycoside synthesis, 1,3-dipolar cycloaddition and reductive cleavage of benzylidene, commonly used in the synthesis of carbohydrate derivatives was examined. A series of glycosylation reactions that employ thioglycosides, glycosyl trichloroacetimidate, glycosyl bromide and glycosyl acetate as the glycosyl donors was also examined. Our results demonstrate that sonication can significantly shorten the reaction time, enhance the reactivity of reactant and lead to superior yield and excellent stereoselectivity. More importantly, a general protocol of glycosylation may finally be developed. Sonication is compatible to the conditions used for traditional organic synthesis. We believe that sonication can also be applied to other areas of synthetic processes.