[(2R,3S,4R,5R,6S)-5-acetamido-6-[[(1R,2S,3R,4R,5R)-4-acetamido-3-hydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-3,4-diacetyloxyoxan-2-yl]methyl acetate | 1228176-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5R,6S)-5-acetamido-6-[[(1R,2S,3R,4R,5R)-4-acetamido-3-hydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-3,4-diacetyloxyoxan-2-yl]methyl acetate
• CAS: 1228176-40-6
• 化学式: C₂₂H₃₂N₂O₁₃
• 分子量: 532.502
• InChiKey: CJYCKFISIKOAPN-MVEDJEFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  194
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  dodecyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 、 [(2R,3S,4R,5R,6S)-5-acetamido-6-[[(1R,2S,3R,4R,5R)-4-acetamido-3-hydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-3,4-diacetyloxyoxan-2-yl]methyl acetate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以74%的产率得到
  参考文献：
  名称：

  Synthetic construction of a fucosyl chitobiose as an allergen-associated carbohydrate epitope and the glycopolymer involving highly clustered trisaccharidic sequences

  摘要：

  Synthetic construction of fucosyl chitobiose [GlcNAc beta 1 -> 4(Fuc alpha 1 -> 3)GlcNAc] as an allergy-associated carbohydrate epitope was accomplished from three building blocks. The trisaccharidic unit was further transformed into a carbohydrate monomer and polymerization of the glycomonomer proceeded smoothly to provide a series of glycopolymers having various carbohydrate densities. In addition to the organic syntheses, biological evaluations of the glycomonomer and the polymers were carried out and sugar-clustering effects were observed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.004
• 作为产物：
  描述：

  2-Acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose 在 1% Pd/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以100%的产率得到[(2R,3S,4R,5R,6S)-5-acetamido-6-[[(1R,2S,3R,4R,5R)-4-acetamido-3-hydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-3,4-diacetyloxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthetic construction of a fucosyl chitobiose as an allergen-associated carbohydrate epitope and the glycopolymer involving highly clustered trisaccharidic sequences

  摘要：

  Synthetic construction of fucosyl chitobiose [GlcNAc beta 1 -> 4(Fuc alpha 1 -> 3)GlcNAc] as an allergy-associated carbohydrate epitope was accomplished from three building blocks. The trisaccharidic unit was further transformed into a carbohydrate monomer and polymerization of the glycomonomer proceeded smoothly to provide a series of glycopolymers having various carbohydrate densities. In addition to the organic syntheses, biological evaluations of the glycomonomer and the polymers were carried out and sugar-clustering effects were observed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.004