(2R,3R,4R,5R,6S)-5-azido-6-(((2R,3R,4R,5R,6S)-5-azido-2-(azidomethyl)-4-(benzyloxy)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)-2-((1,3-dioxoisoindolin-2-yl)methyl)tetrahydro-2H-pyran-3-yl acetate | 1379976-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R,6S)-5-azido-6-(((2R,3R,4R,5R,6S)-5-azido-2-(azidomethyl)-4-(benzyloxy)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)-2-((1,3-dioxoisoindolin-2-yl)methyl)tetrahydro-2H-pyran-3-yl acetate
• CAS: 1379976-86-9
• 化学式: C₃₇H₃₈N₁₀O₁₀
• 分子量: 782.77
• InChiKey: MHRQZUFNQWZFJC-GLNRYMJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  57.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  265.34
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  Methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 sodium azide 、 三氟甲磺酸 、 水 、 溶剂黄146 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 methyl (4-O-acetyl-2-azido-2-deoxy-3-O-benzyl-6-deoxy-6-phthalimido-α-D-glucopyranosyl)-(1->4)-2,6-diazido-2,6-dideoxy-3-O-benzyl-α-D-glucopyranoside 、 (2R,3R,4R,5R,6S)-5-azido-6-(((2R,3R,4R,5R,6S)-5-azido-2-(azidomethyl)-4-(benzyloxy)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)-2-((1,3-dioxoisoindolin-2-yl)methyl)tetrahydro-2H-pyran-3-yl acetate
  参考文献：
  名称：

  Synthesis of Oligodiaminosaccharides Having α-Glycoside Bonds and Their Interactions with Oligonucleotide Duplexes

  摘要：

  Syntheses of the novel oligodiaminosaccharides, alpha-(1 -> 4)linked-2,6-diamino-2,6-dideoxy-D-glucopyranose oligomers, and their interactions with nucleic acid duplexes DNA-DNA, RNA-RNA, and DNA-RNA are described. Monomers to tetramers of oligodiaminoglucose derivatives having alpha-glycosyl bonds were successfully synthesized using a chain elongation cycle including glycosylation reactions of a 6-phthalimide glycosyl donor. UV melting experiments for a variety of nucleic acid duplexes in the absence and presence of the oligodiaminosaccharides were performed. The synthesized oligodiaminosaccharides exhibited notable thermodynamic stabilization effects on A-type RNA-RNA and DNA-RNA duplexes, whereas B-type DNA-DNA duplexes were not stabilized by the synthesized oligodiaminosaccharides. Among the oligodiaminosaccharides, the tetramer exhibited the highest ability to stabilize A-type duplexes, and the increase in T(m) values induced by the tetramer were higher than those induced by neomycin B and tobramycin, which are known aminoglycosides having ability to bind and stabilize a variety of RNA molecules. CD spectrometry experiments revealed that the oligodiaminosaccharides caused small structural changes in RNA-RNA duplexes, whereas no appreciable changes were observed in the structure of DNA-DNA duplexes. ITC (isothermal titration calorimetry) experiments demonstrated that the amount of heat generated by the interaction between RNA-RNA duplexes and the tetradiaminosaccharides was approximately double that generated by that between DNA-DNA duplexes and the tetradiaminosaccharides. These results strongly suggested the existence of an A-type nucleic acid specific-binding mode of the oligodiaminosaccharides, which bind to these duplexes and cause small structural changes.

  DOI：

  10.1021/jo200951p