p-nitrophenyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-xylo-hexopyranoside | 23655-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-xylo-hexopyranoside
• CAS: 23655-56-3
• 化学式: C₁₈H₂₁NO₁₀
• 分子量: 411.365
• InChiKey: CLQIYYCYEALTJN-ZJPYXAASSA-N

物化性质

• 沸点：
  534.7±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140.5
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-xylo-hexopyranoside 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以90.9%的产率得到p-nitrophenyl 2-deoxy-α-D-xylo-hexopyranoside
  参考文献：
  名称：

  Hydrolytic activity of α-galactosidases against deoxy derivatives of p-nitrophenyl α-d-galactopyranoside

  摘要：

  The four possible monodeoxy derivatives of p-nitrophenyl (PNP) alpha-D-galactopyranoside were synthesized, and hydrolytic activities of the alpha-galactosidase of green coffee bean, Mortierella vinacea and Aspergillus niger against them were elucidated. The 2- and 6-deoxy substrates were hydrolyzed by the enzymes from green coffee bean and M. vinacea, while they scarcely acted on the 3- and 4-deoxy compounds. On the other hand, A. niger alpha-galactosidase hydrolyzed only the 2-deoxy compound in these deoxy substrates, and the activity was very high. These results indicate that the presence of two hydroxyl groups (OH-3 and -4) is essential for the compounds to act as substrates for the enzymes of green coffee bean and M. vinacea, while the three hydroxyl groups (OH-3, -4, and -6) are necessary for the activity of the A. niger enzyme. The kinetic parameters (K-m and V-max) of the enzymes for the hydrolysis of PNP alpha-D-galactopyranoside and its deoxy derivatives were obtained from kinetic studies. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00281-5
• 作为产物：
  描述：

  1,2,3,4,6-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 、 氢溴酸 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 、 苯 为溶剂， 反应 24.0h， 生成 p-nitrophenyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-xylo-hexopyranoside
  参考文献：
  名称：

  Hydrolytic activity of α-galactosidases against deoxy derivatives of p-nitrophenyl α-d-galactopyranoside

  摘要：

  The four possible monodeoxy derivatives of p-nitrophenyl (PNP) alpha-D-galactopyranoside were synthesized, and hydrolytic activities of the alpha-galactosidase of green coffee bean, Mortierella vinacea and Aspergillus niger against them were elucidated. The 2- and 6-deoxy substrates were hydrolyzed by the enzymes from green coffee bean and M. vinacea, while they scarcely acted on the 3- and 4-deoxy compounds. On the other hand, A. niger alpha-galactosidase hydrolyzed only the 2-deoxy compound in these deoxy substrates, and the activity was very high. These results indicate that the presence of two hydroxyl groups (OH-3 and -4) is essential for the compounds to act as substrates for the enzymes of green coffee bean and M. vinacea, while the three hydroxyl groups (OH-3, -4, and -6) are necessary for the activity of the A. niger enzyme. The kinetic parameters (K-m and V-max) of the enzymes for the hydrolysis of PNP alpha-D-galactopyranoside and its deoxy derivatives were obtained from kinetic studies. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00281-5

文献信息

• Facile TMSOTf-catalyzed preparation of 2-deoxy α-O-aryl-D-glycosides from glycosyl acetates
  作者：Guofang Yang、Qingbing Wang、Xiaosheng Luo、Jianbo Zhang、Jie Tang

  DOI：10.1007/s10719-012-9429-7

  日期：2012.8

  2-Deoxy α-O-aryl glycosides were conveniently obtained by reaction of 2-deoxy-glycosyl acetates with phenols in the presence of TMSOTf as the promoter. The current method provides the O-aryl glycosides with good to excellent yields, and sole alpha selectivity.

  在以 TMSOTf 为促进剂的存在下，通过 2-脱氧-糖基乙酸酯与苯酚的反应，可以方便地获得 2-脱氧 α-O-芳基苷。目前的方法可以提供良好到极佳收率的 O-芳基苷，并具有唯一的α选择性。