(2,4,6-tri-O-acetyl-3-O-(4-phenoxybenzyl)-β-D-galactopyranosyl)-β-(1,4)6-O-acetyl-2-deoxy-2-N-phthalimido-3-azidopropyl-β-D-glucopyranoside | 1421638-27-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,4,6-tri-O-acetyl-3-O-(4-phenoxybenzyl)-β-D-galactopyranosyl)-β-(1,4)6-O-acetyl-2-deoxy-2-N-phthalimido-3-azidopropyl-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-6-(3-azidopropoxy)-3-[(2S,3R,4S,5S,6R)-3,5-diacetyloxy-6-(acetyloxymethyl)-4-[(4-phenoxyphenyl)methoxy]oxan-2-yl]oxy-5-(1,3-dioxoisoindol-2-yl)-4-hydroxyoxan-2-yl]methyl acetate
• CAS: 1421638-27-8
• 化学式: C₄₄H₄₈N₄O₁₇
• 分子量: 904.882
• InChiKey: QDQHWYODWXJOHH-XFMMKEFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  65
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  233
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  (2,4,6-tri-O-acetyl-3-O-(4-phenoxybenzyl)-β-D-galactopyranosyl)-β-(1,4)6-O-acetyl-2-deoxy-2-N-phthalimido-3-azidopropyl-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 6.0h， 以73%的产率得到(3-O-(4-phenoxybenzyl)-β-D-galactopyranosyl)-β-(1,4)-2-deoxy-2-N-phthalimido-3-azidopropyl-β-D-glucopyranoside
  参考文献：
  名称：

  Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1

  摘要：

  Inhibitors for galectin-1 and -3 were synthesized from thiodigalactoside and lactosamine by derivatization of the galactose C3. Introduction of 4-phenyl-1H-1,2,3-triazol-1-yl substituents at the thiodigalactoside C3 by CuAAC, targeting arginine-arene interactions, increased the affinity to 13 nM but yielded little selectivity. The builder 4-(4-phenoxypheny1)-1H-1,2,3-triazol-1-yl substituent, however, increased the preference for galectin-3 over galectin-1 to more than 200-fold. Modeling showed more arginine-arene interactions for galectin-3 than for galectin-1. Introducing 4-phenoxyaryl groups on lactosamine had a similar effect.

  DOI：

  10.1021/jm301677r
• 作为产物：
  描述：

  3-azidopropyl 2-deoxy-2-N-phthalimido-β-D-glucopyranoside 在 2,4,6-三甲基吡啶 、 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.25h， 生成 (2,4,6-tri-O-acetyl-3-O-(4-phenoxybenzyl)-β-D-galactopyranosyl)-β-(1,4)6-O-acetyl-2-deoxy-2-N-phthalimido-3-azidopropyl-β-D-glucopyranoside
  参考文献：
  名称：

  Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1

  摘要：

  Inhibitors for galectin-1 and -3 were synthesized from thiodigalactoside and lactosamine by derivatization of the galactose C3. Introduction of 4-phenyl-1H-1,2,3-triazol-1-yl substituents at the thiodigalactoside C3 by CuAAC, targeting arginine-arene interactions, increased the affinity to 13 nM but yielded little selectivity. The builder 4-(4-phenoxypheny1)-1H-1,2,3-triazol-1-yl substituent, however, increased the preference for galectin-3 over galectin-1 to more than 200-fold. Modeling showed more arginine-arene interactions for galectin-3 than for galectin-1. Introducing 4-phenoxyaryl groups on lactosamine had a similar effect.

  DOI：

  10.1021/jm301677r