(3-trifluoroacetamidopropyl)-2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-4-O-[2,4-di-O-acetyl-6-O-benzyl-3-O-(2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside | 1155352-42-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-trifluoroacetamidopropyl)-2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-4-O-[2,4-di-O-acetyl-6-O-benzyl-3-O-(2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside
• CAS: 1155352-42-3
• 化学式: C₅₆H₇₀F₃N₃O₂₁
• 分子量: 1178.17
• InChiKey: OHWYPVRJRBSKGL-MJZGTRAASA-N

物化性质

• 沸点：
  1128.0±65.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  83.0
• 可旋转键数：
  27.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  295.8
• 氢给体数：
  4.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  (3-trifluoroacetamidopropyl)-2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-4-O-[2,4-di-O-acetyl-6-O-benzyl-3-O-(2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside 、 2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranosyl bromide 在 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到(3-trifluoroacetamidopropyl)-2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-4-O-{2,4-di-O-acetyl-6-O-benzyl-3-O-[2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-4-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-β-D-galactopyranosyl}-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of linear trilactosamine

  摘要：

  TrilactosamineGal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta-sp, where sp = O(CH(2))(3)NH(2) is a spacer, was synthesized. The tetrasaccharide fragment Gal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta-sp was obtained by successive glycosylation using elongation by one monosaccharide residue at a time; and the tetrasaccharide was then transformed into a hexasaccharide with a disaccharide glycosyl donor. A 2,2,2-trichloroethoxycarbonyl group was used for the protection of the glucosamine amino group.

  DOI：

  10.1134/s1068162008050129
• 作为产物：
  描述：

  (3-trifluoroacetamidopropyl)-2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-4-O-[2,4-di-O-acetyl-6-O-benzyl-3-O-(2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以91%的产率得到(3-trifluoroacetamidopropyl)-2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-4-O-[2,4-di-O-acetyl-6-O-benzyl-3-O-(2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of linear trilactosamine

  摘要：

  TrilactosamineGal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta-sp, where sp = O(CH(2))(3)NH(2) is a spacer, was synthesized. The tetrasaccharide fragment Gal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta-sp was obtained by successive glycosylation using elongation by one monosaccharide residue at a time; and the tetrasaccharide was then transformed into a hexasaccharide with a disaccharide glycosyl donor. A 2,2,2-trichloroethoxycarbonyl group was used for the protection of the glucosamine amino group.

  DOI：

  10.1134/s1068162008050129