(2R,2'R,3S,3'S,4R,4'R,5R,5'R,6R,6'R)-((2-(ethoxycarbonyl)-2-nitropropane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-6,3,4-triyl) tetraacetate | 1476079-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,2'R,3S,3'S,4R,4'R,5R,5'R,6R,6'R)-((2-(ethoxycarbonyl)-2-nitropropane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-6,3,4-triyl) tetraacetate
• CAS: 1476079-69-2
• 化学式: C₃₈H₅₁N₉O₂₀
• 分子量: 953.871
• InChiKey: RTEHYIZEPFOYOB-OCHPSTKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.11
• 重原子数：
  67.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  365.32
• 氢给体数：
  2.0
• 氢受体数：
  26.0

反应信息

• 作为产物：
  描述：

  ethyl 2,2-bis(propargyl)-2-nitroacetate 、 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖酰基叠氮化物 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以86%的产率得到(2R,2'R,3S,3'S,4R,4'R,5R,5'R,6R,6'R)-((2-(ethoxycarbonyl)-2-nitropropane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-6,3,4-triyl) tetraacetate
  参考文献：
  名称：

  Synthesis of divalent glycoamino acids with bis-triazole linkage

  摘要：

  Triazole-linked diversely functionalized divalent glycoconjugates were synthesized using Cu(I) catalyzed [3+2] cycloaddition reaction of the desired azides and alkynes. A series of per-O-acetylated glycopyranosyl azides and per-O-acetylated glucopyranosyl azidoacetamide were reacted with nitro- and cyano-functionalized dialkyne building blocks as precursors of alpha- and beta-amino acids, respectively. To introduce more conformational flexibility in the divalent molecules, peptoid-based triazole-linked divalent glycoconjugate was also synthesized. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.006