tris-{2-[(6'-deoxy-1'-O-methyl-α-D-mannopyranos-6'-yl)carbamoyl]ethyl}-nitromethane | 211985-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tris-{2-[(6'-deoxy-1'-O-methyl-α-D-mannopyranos-6'-yl)carbamoyl]ethyl}-nitromethane
• 英文别名: 4-nitro-4-[3-oxo-3-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methylamino]propyl]-N,N'-bis[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]heptanediamide
• CAS: 211985-70-5
• 化学式: C₃₁H₅₄N₄O₂₀
• 分子量: 802.785
• InChiKey: LELGBZXCEYHZNN-MZIKOMLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  371
• 氢给体数：
  12
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  tris-{2-[(6'-deoxy-1'-O-methyl-α-D-mannopyranos-6'-yl)carbamoyl]ethyl}-nitromethane 在 palladium on activated charcoal 氢气 、 ammonium formate 作用下， 以 甲醇 为溶剂， 反应 30.0h， 以79%的产率得到tris-{2-[(6'-deoxy-1'-O-methyl-α-D-mannopyranos-6'-yl)carbamoyl]ethyl}-aminomethane
  参考文献：
  名称：

  Multivalent glycomimetics: synthesis of nonavalent mannoside clusters with variation of spacer properties

  摘要：

  Oligosaccharide mimetics are important tools in the glycosciences. In this work, we have employed spaced glycodendrons for the synthesis of oligomannoside mimetics. Starting from a number of trivalent, branched molecular wedges, the preparation of nonavalent cluster mannosides was accomplished, which were varied with regard to the chemical characteristics of their spacer moieties and spacer lengths. For ligation of the various trivalent dendrons to the nonavalent target molecules peptide coupling was employed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.024
• 作为产物：
  描述：

  nitrotris-{2-[(2',3',4'-tri-O-benzoyl-6'-deoxy-1'-O-methyl-α-D-mannopyranos-6'-yl)carbamoyl]ethyl}methane 在 sodium methylate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 48.0h， 以98%的产率得到tris-{2-[(6'-deoxy-1'-O-methyl-α-D-mannopyranos-6'-yl)carbamoyl]ethyl}-nitromethane
  参考文献：
  名称：

  Multivalent ligands for the mannose-specific lectin on type 1 fimbriae of Escherichia coli : syntheses and testing of trivalent α-D-mannoside clusters

  摘要：

  描述了三触角簇α-D-甘露糖苷16、19、23和24的合成及其抑制大肠杆菌HB 101 (pPK14)的甘露糖依赖性结合的能力。簇糖苷是通过三-(3-羟丙基)硝基甲烷 13 的糖基化，以及通过酰胺键和硫脲键将合适的甘露糖苷衍生物与三-(2-羧乙基)硝基甲烷 17 和三-(2-氨基乙基)胺 20 连接而形成的功能化甘露糖苷附着在糖环 6 位的核心分子上，以允许引入的糖苷配基部分发生变化，以便比较它们对衍生甘露糖苷簇的抑制效力的影响。通过抑制凝集试验和 ELISA 测试，6 肽桥簇甘露糖苷 19 对大肠杆菌 1 型菌毛凝集素显示出最高的结合效力。

  DOI：

  10.1039/a801985a

文献信息

• Multivalent glycomimetics: synthesis of nonavalent mannoside clusters with variation of spacer properties
  作者：Anupama Patel、Thisbe K. Lindhorst

  DOI：10.1016/j.carres.2006.01.024

  日期：2006.7

  Oligosaccharide mimetics are important tools in the glycosciences. In this work, we have employed spaced glycodendrons for the synthesis of oligomannoside mimetics. Starting from a number of trivalent, branched molecular wedges, the preparation of nonavalent cluster mannosides was accomplished, which were varied with regard to the chemical characteristics of their spacer moieties and spacer lengths. For ligation of the various trivalent dendrons to the nonavalent target molecules peptide coupling was employed. (c) 2006 Elsevier Ltd. All rights reserved.
• Multivalent ligands for the mannose-specific lectin on type 1 fimbriae of Escherichia coli : syntheses and testing of trivalent α-D-mannoside clusters
  作者：Sven Kötter、Ulrike Krallmann-Wenzel、Stefan Ehlers、Thisbe K. Lindhorst

  DOI：10.1039/a801985a

  日期：——

  The syntheses of the triantennary cluster α-D-mannosides 16, 19, 23 and 24 and their capacities to inhibit mannose-dependent binding of E. coli HB 101 (pPKl4) are described. The cluster glycosides are formed by glycosylation of tris-(3-hydroxypropyl)nitromethane 13, and by linking of suitable mannoside derivatives via amide and thiourea bonds to tris-(2-carboxyethyl)nitromethane 17 and tris-(2-aminoethyl)amine 20. Functionalized mannosides are attached to the core molecules at the 6-position of the sugar ring to allow variation of the introduced aglycone moieties in order to compare their effects on the inhibitory potencies of the derived mannoside clusters. The 6-peptide-bridged cluster mannoside 19 displays the highest binding potency towards the type 1 fimbrial lectin of E. coli as tested by inhibition agglutination tests and ELISA.

  描述了三触角簇α-D-甘露糖苷16、19、23和24的合成及其抑制大肠杆菌HB 101 (pPK14)的甘露糖依赖性结合的能力。簇糖苷是通过三-(3-羟丙基)硝基甲烷 13 的糖基化，以及通过酰胺键和硫脲键将合适的甘露糖苷衍生物与三-(2-羧乙基)硝基甲烷 17 和三-(2-氨基乙基)胺 20 连接而形成的功能化甘露糖苷附着在糖环 6 位的核心分子上，以允许引入的糖苷配基部分发生变化，以便比较它们对衍生甘露糖苷簇的抑制效力的影响。通过抑制凝集试验和 ELISA 测试，6 肽桥簇甘露糖苷 19 对大肠杆菌 1 型菌毛凝集素显示出最高的结合效力。