4-aminophenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside | 17306-77-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-aminophenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
• 英文别名: p-Aminophenyl-tri-O-acetyl-β-D-xylopyranosid；[(3R,4S,5R,6S)-4,5-diacetyloxy-6-(4-aminophenoxy)oxan-3-yl] acetate
• CAS: 17306-77-3
• 化学式: C₁₇H₂₁NO₈
• 分子量: 367.356
• InChiKey: BZOUELJEVWYTIL-TWMKSMIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-aminophenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 在 亚硝酸特丁酯 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以100%的产率得到4-(2,3,4-tri-O-acetyl-β-D-xylopyranosyloxy)phenyldiazonium tetrafluoroborate
  参考文献：
  名称：

  Synthesis of Amphiphilic Phenylazophenyl Glycosides and a Study of Their Liquid Crystal Properties

  摘要：

  Several 4-(4'-N,N-didodecylaminophenylazo)phenyl 1,2-trans glycosides 5a-e with various carbohydrate heads (beta-D-gluco, beta-D-galacto, beta-lacto, beta-D-xylo, and alpha-D-manno) have been synthesized. The key step was the formation of phenyldiazonium tetrafluoroborates 2a-e from the per-O-acetylated 4-aminophenyl glycosides 1a-e. These salts were condensed with N,N-didoclecylaniline under phase transfer conditions and the per-O-acetylated 4-(4'-N,N-didodecylaminophenylazo)phenyl 1,2-trans glycosides 4a-e were fully de-O-acetylated by the Zemplen method. The self-organizing liquid crystal properties of the compounds were investigated by a variety of techniques, including polarized light microscopy, differential scanning calorimetry, and X-ray diffraction. All but one of the materials exhibited smectic A, lamellar phases. Remarkably, the glucose derivative exhibited a rectangular disordered columnar phase. This result has implications with respect to the induced curvature created by the recognition processes of the glucose headgroup relative to the other sugar moieties and to the prevalence of various glycolipids in cell membranes.

  DOI：

  10.1021/ja037347x
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide 在 palladium 10% on activated carbon 、 四丁基溴化铵 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 、 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 4-aminophenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  2,6-二取代嘌呤衍生物的合成及抑菌活性的评价

  摘要：

  由2,6-二氯嘌呤设计并合成了一系列新颖的2,6-二取代嘌呤衍生物。目标化合物的结构由1 H-NMR，13 C-NMR和HRMS确定。评估了合成的化合物对A549肺癌细胞系和Bel-7402肝癌细胞系的抑制活性。2-（4-苄氧基-苯基氨基）-6-（环己基氨基）嘌呤（3），2-（4-氯-苯基氨基）-6-（正丁基氨基）嘌呤（5），2-（4-吗啉代氨基）- 6-（4-羟基-苯基氨基）嘌呤（9）和2-（4 - O-半乳糖基-苯基氨基）-6-（环己基氨基）嘌呤（12）表现出中等的抑制活性。

  DOI：

  10.1002/jhet.1959