6,6'-diamino-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose | 76790-48-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6'-diamino-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose
• 英文别名: 6,6'-diamino-2,2',3,3',4,4'-hexa-O-benzyl-6,6'-dideoxy-α-D-trehalose；6,6'-diamino-2,3,4,2',3',4'-hexabenzyloxy-α,α'-trehalose；[(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-(aminomethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanamine
• CAS: 76790-48-2
• 化学式: C₅₄H₆₀N₂O₉
• 分子量: 881.078
• InChiKey: UGHIYFGAWQYQPN-IPCGEZBZSA-N

物化性质

• 沸点：
  913.3±65.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  65
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6,6'-diamino-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose 在 palladium dihydroxide 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 6,6'-dioctylcarbamoylamino-6,6'-dideoxy-α-D-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-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranosyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranoside 在 sodium hydroxide 、 sodium azide 、 三甲基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 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

文献信息

• TREHALOSE COMPOUND, PROCESS FOR PRODUCTION OF THE COMPOUND, AND IMMUNO-STIMULATIVE AGENT COMPRISING THE COMPOUND
  申请人：GLYTECH, INC.

  公开号：EP2123662B1

  公开（公告）日：2013-12-04
• 6,6′-Diamino-2,3,4,2′,3′,4′-hexa-O-benzyl 6,6′-dideoxy-α,α-trehalose
  作者：Avraham Liav、Mayer B. Goren

  DOI：10.1016/s0008-6215(00)85200-3

  日期：1980.12
• First synthesis of bridged and double calixsugars
  作者：Alessandro Dondoni、Xubo Hu、Alberto Marra、Harold D Banks

  DOI：10.1016/s0040-4039(01)00433-6

  日期：2001.5

  Bridged and double calixarene-trehalose molecular architectures have been assembled through ester and amide linkages between the sugar and the macrocycle units; the double calixsugar showed selective receptor properties toward imidazole. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Diamide pseudo cord-factors: bis-N-acyl derivatives of 6,6′-diamino-6,6′-dideoxy-α,α-trehalose
  作者：Avraham Liav、Bhupesh C. Das、Mayer B. Goren

  DOI：10.1016/s0008-6215(00)80721-1

  日期：1981.8
• Synthesis of trehalose-based compounds and their inhibitory activities against Mycobacterium smegmatis
  作者：Jinhua Wang、Bryan Elchert、Yu Hui、Jon Y. Takemoto、Mekki Bensaci、John Wennergren、Huiwen Chang、Ravi Rai、Cheng-Wei Tom Chang

  DOI：10.1016/j.bmc.2004.09.033

  日期：2004.12

  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.