6,6'-N,N'-bis[6,6'-bis-benzamido-6,6'-dideoxy-β-maltosyl-(1-6)-D-galactit-1-yl]-6,6'-dideoxy-6,6'-dimethylamino-β-maltosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 293298-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6'-N,N'-bis[6,6'-bis-benzamido-6,6'-dideoxy-β-maltosyl-(1-6)-D-galactit-1-yl]-6,6'-dideoxy-6,6'-dimethylamino-β-maltosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: N-[[(2R,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-2-(benzamidomethyl)-6-[(2R,3S,4R,5S)-6-[[(2R,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-2-[[[(2S,3R,4S,5R)-6-[(2R,3R,4R,5S,6R)-6-(benzamidomethyl)-5-[(2R,3R,4S,5S,6R)-6-(benzamidomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-2,3,4,5-tetrahydroxyhexyl]-methylamino]methyl]-4,5-dihydroxy-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl-methylamino]-2,3,4,5-tetrahydroxyhexoxy]-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl]benzamide
• CAS: 293298-92-7
• 化学式: C₉₀H₁₃₀N₆O₄₄
• 分子量: 2000.04
• InChiKey: FYUPHIDHZXSLOY-TVWWVZHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10
• 重原子数：
  140
• 可旋转键数：
  41
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  745
• 氢给体数：
  27
• 氢受体数：
  46

反应信息

• 作为反应物：
  描述：

  6,6'-N,N'-bis[6,6'-bis-benzamido-6,6'-dideoxy-β-maltosyl-(1-6)-D-galactit-1-yl]-6,6'-dideoxy-6,6'-dimethylamino-β-maltosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 三氟乙酸 作用下， 反应 0.25h， 以60%的产率得到6,6'-N,N'-bis[6,6'-bisbenzamido-6,6'-dideoxy-β-maltosyl-(1-6)-D-galactit-1-yl]-6,6'-dideoxy-6,6'-dimethylamino-β-maltosyl-(1-6)-D-galactose
  参考文献：
  名称：

  Large Oligosaccharide-Based Glycodendrimers Synthetic Carbohydrate Dendrimers, Part 9: for Part 8, see: W. B. Turnbull, A. R. Pease, J. F. Stoddart, ChemBioChem 2000, 1, 70–74.

  摘要：

  Carbohydrate-based dendritic structures composed of 21 and 27 monosaccharide residues have been synthesized in a convergent manner from trisaccharide building blocks. The oligosaccharide AB, monomers are based on a maltosylbeta(1 --> 6)galactose structure, which has been modified to include two methylamino groups at the primary positions of the glucosyl residues. Reductive alkylation of the secondary amino groups, with the innate formyl function of a second oligosaccharide monomer, allows for the chemoselective construction of dendritic wedges. while employing a minimal number of protecting groups. The first-generation dendron can be coupled either to another AB? monomer, to give a second-generation dendron, or to a tris[2-(methylamino)ethyl] a mine-based core moiety, to provide a carbohydrate-based dendrimer. Alternating alpha- and beta-glucosyl residues in the monomers and dendrons, simplifies H-1 NMR spectra as a consequence of spreading out the anomeric proton signals. Monomers and dendrons were characterized by extensive one- and two-dimensional NMR spectroscopy in addition to FAB, electrospray, and MALDI-TOF mass spectrometry. Molecular dynamics simulations revealed similar conformations in the dendrons as in the isolated trisaccharide repeating units.

  DOI：

  10.1002/1521-3765(20020703)8:13<2988::aid-chem2988>3.0.co;2-2
• 作为产物：
  描述：

  6-deoxy-6-N-methylamino-α-D-glucopyranosyl-(1-4)-6-deoxy-6-methylamino-β-D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 、 6-benzamido-6-deoxy-α-D-glucopyranosyl-(1-4)-6-benzamido-6-deoxy-β-D-glucopyranosyl-(1-6)-α-D-galactose 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 6,6'-N,N'-bis[6,6'-bis-benzamido-6,6'-dideoxy-β-maltosyl-(1-6)-D-galactit-1-yl]-6,6'-dideoxy-6,6'-dimethylamino-β-maltosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Large Oligosaccharide-Based Glycodendrimers Synthetic Carbohydrate Dendrimers, Part 9: for Part 8, see: W. B. Turnbull, A. R. Pease, J. F. Stoddart, ChemBioChem 2000, 1, 70–74.

  摘要：

  Carbohydrate-based dendritic structures composed of 21 and 27 monosaccharide residues have been synthesized in a convergent manner from trisaccharide building blocks. The oligosaccharide AB, monomers are based on a maltosylbeta(1 --> 6)galactose structure, which has been modified to include two methylamino groups at the primary positions of the glucosyl residues. Reductive alkylation of the secondary amino groups, with the innate formyl function of a second oligosaccharide monomer, allows for the chemoselective construction of dendritic wedges. while employing a minimal number of protecting groups. The first-generation dendron can be coupled either to another AB? monomer, to give a second-generation dendron, or to a tris[2-(methylamino)ethyl] a mine-based core moiety, to provide a carbohydrate-based dendrimer. Alternating alpha- and beta-glucosyl residues in the monomers and dendrons, simplifies H-1 NMR spectra as a consequence of spreading out the anomeric proton signals. Monomers and dendrons were characterized by extensive one- and two-dimensional NMR spectroscopy in addition to FAB, electrospray, and MALDI-TOF mass spectrometry. Molecular dynamics simulations revealed similar conformations in the dendrons as in the isolated trisaccharide repeating units.

  DOI：

  10.1002/1521-3765(20020703)8:13<2988::aid-chem2988>3.0.co;2-2