2,2',3,3',4,4'-hexa-O-benzoyl-6,6'-bis-O-((trifluoromethyl)sulfonyl)-α,α'-trehalose | 142386-47-8

• 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: 2,2',3,3',4,4'-hexa-O-benzoyl-6,6'-bis-O-((trifluoromethyl)sulfonyl)-α,α'-trehalose
• 英文别名: 2,3,4,2',3',4'-hexa-O-benzoyl-6,6'-O-trifluoromethanesulfonyl-α,α-trehalose；2,2',3,3',4,4'-hexa-O-benzoyl-6,6'-bis-O-[(trifluoromethyl)sulfonyl]-α,α'-trehalose
• CAS: 142386-47-8
• 化学式: C₅₆H₄₄F₆O₂₁S₂
• 分子量: 1231.08
• InChiKey: BMLHOLXVRASJJE-YBWLRKLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.54
• 重原子数：
  85.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  272.23
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  2,2',3,3',4,4'-hexa-O-benzoyl-6,6'-bis-O-((trifluoromethyl)sulfonyl)-α,α'-trehalose 在 platinum(IV) oxide 氢气 、 sodium methylate 、 sodium cyanoborohydride 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 、 水 、 乙腈 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 141.0h， 生成 6,6'-dideoxy-6,6'-bis{[1-(hydroxymethyl)propyl]methyl}-α,α-trehalose
  参考文献：
  名称：

  Ethambutol–sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis

  摘要：

  Ethambutol is an established front-line agent for the treatment of tuberculosis, and is also active against Mycobacterium avium infection. However, this agent exhibits toxicity, and is considered to have low potency. The action of ethambutol on the mycobacterial cell wall, particularly the arabinan, and comparison of the structure of ethambutol with several of the cell-wall saccharides, suggested that ethambutol-saccharide hybrids might lead to agents with a more selective mechanism of action. To this end, eight ethambutol-saccharide hybrids were synthesized and screened against M. tuberculosis and several clinical isolates of M. avium. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00069-5
• 作为产物：
  描述：

  三氟甲磺酸酐 、 2,2',3,3',4,4'-hexa-O-benzoyl-α,α'-trehalose 在 2,6-二叔丁基-4-甲基苯酚 作用下， 以 二氯甲烷 为溶剂， 生成 2,2',3,3',4,4'-hexa-O-benzoyl-6,6'-bis-O-((trifluoromethyl)sulfonyl)-α,α'-trehalose
  参考文献：
  名称：

  一类新的由α，α'-海藻糖形成的中性手性环烷

  摘要：

  一类新的手性环芳的合成和初步研究络合1 - 6，具有比得上环糊精和环芳特性，进行说明。

  DOI：

  10.1039/c39920000683

文献信息

• Glycophanes, cyclodextrin-cyclophane hybrid receptors for apolar binding in aqueous solutions. A stereoselective carbohydrate-carbohydrate interaction in water
  作者：Jose M. Coteron、Cristina Vicent、Claude Bosso、Soledad Penades

  DOI：10.1021/ja00075a023

  日期：1993.11

  because carbohydrate molecules, lipophilic cavities, and aromatic interactions are involved. They are built from α,α'-trehalose and 2,7-dihydroxynaphthalene or 4,4'-isopropylidenediphenol. The water soluble glycophane 12 displays a general affinity for electron-deficient aromatic guests (nitro derivatives of phenol and benzenesulfonic and benzenecarboxylic acids), the association constants increasing with

  报道了一种新型中性手性受体糖芬 4-6 和 9-14 的合成和络合特性。它们可以被认为是环糊精-环烷杂化物，因为涉及碳水化合物分子、亲脂腔和芳香相互作用。它们由 α,α'-海藻糖和 2,7-二羟基萘或 4,4'-异亚丙基二酚构成。水溶性甘聚糖 12 显示出对缺电子芳香客体（苯酚和苯磺酸和苯羧酸的硝基衍生物）的普遍亲和力，结合常数随着吸电子基团 (NO 2 ) 数量的增加而增加。根据溶剂，不同的因素似乎有助于配合物的稳定性
• Synthesis and biological evaluation of trehalose analogs as potential inhibitors of mycobacterial cell wall biosynthesis
  作者：Jerry D. Rose、Joseph A. Maddry、Robert N. Comber、William J. Suling、Larry N. Wilson、Robert C. Reynolds

  DOI：10.1016/s0008-6215(01)00288-9

  日期：2002.2

  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.