3-O-<2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl>-D-galactopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-<2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl>-D-galactopyranose
• 英文别名: beta-D-Gal-(1->4)-beta-D-GlcNAc-(1->3)-D-Gal；N-[(2S,3R,4R,5S,6R)-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(3R,4S,5S,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl]oxyoxan-3-yl]acetamide
• 化学式: C₂₀H₃₅NO₁₆
• 分子量: 545.495
• InChiKey: VGVHVNDLCYSGNE-DYAHILLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  278
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  2,2,2-trichloroethyl 3-O-<2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl>-β-D-galactopyranoside 在 锌铜偶 、 溶剂黄146 作用下， 反应 4.0h， 以57%的产率得到3-O-<2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl>-D-galactopyranose
  参考文献：
  名称：

  Syntheses of core chain trisaccharides related to human blood group antigenic determinants

  摘要：

  采用邻苯二甲酰亚胺-氯化物法合成了与人类血型决定因子核心链相关的三糖类化合物，即β-D-Galp-(1 → 3)-β-D-GlcNAcp-(1 → 6)-D-Galp(3)、β-D-Galp-(1 → 3)-β-D-GlcNAcp-(1 → 3)-D-Galp(5)、β-D-Galp-(1 → 4)-β-D-GlcNAcp-(1 → 6)-D-Galp(4)和β-D-Galp-(1 → 4)-β-D-GlcNAcp-(1 → 3)-D-Galp(6)。此外，还报道了这些三糖类化合物的8-甲氧羰基辛基β-糖苷化合物的合成。

  DOI：

  10.1139/v82-012

文献信息

• Synthesis with immobilized enzymes of two trisaccharides, one of them active as the determinant of a stage antigen.
  作者：Claudine Augé、Serge David、Cécile Mathieu、Christine Gautheron

  DOI：10.1016/s0040-4039(01)80188-x

  日期：——
• Syntheses of core chain trisaccharides related to human blood group antigenic determinants
  作者：R. U. Lemieux、S. Z. Abbas、B. Y. Chung

  DOI：10.1139/v82-012

  日期：1982.1.1

  Trisaccharides related to the core chain of human blood group determinants were synthesized by way of the phthalimido-chloride method; namely, β-D-Galp-(1 → 3)-β-D-GlcNAcp-(1 → 6)-D-Galp (3), β-D-Galp-(1 → 3)-β-D-GlcNAcp-(1 → 3)-D-Galp (5), β-D-Galp-(1 → 4)-β-D-GlcNAcp-(1 → 6)-D-Galp (4), and β-D-Galp-(1 → 4)-β-D-GlcNAcp-(1 → 3)-D-Galp (6). The syntheses of the 8-methoxy-carbonyloctyl β-glycosides of these trisaccharides are also reported.

  采用邻苯二甲酰亚胺-氯化物法合成了与人类血型决定因子核心链相关的三糖类化合物，即β-D-Galp-(1 → 3)-β-D-GlcNAcp-(1 → 6)-D-Galp(3)、β-D-Galp-(1 → 3)-β-D-GlcNAcp-(1 → 3)-D-Galp(5)、β-D-Galp-(1 → 4)-β-D-GlcNAcp-(1 → 6)-D-Galp(4)和β-D-Galp-(1 → 4)-β-D-GlcNAcp-(1 → 3)-D-Galp(6)。此外，还报道了这些三糖类化合物的8-甲氧羰基辛基β-糖苷化合物的合成。