p-nitrophenyl 2,3,4-tri-O-acetyl-6-O-methyl-α-D-galactopyranoside | 280136-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2,3,4-tri-O-acetyl-6-O-methyl-α-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-4,5-diacetyloxy-2-(methoxymethyl)-6-(4-nitrophenoxy)oxan-3-yl] acetate
• CAS: 280136-46-1
• 化学式: C₁₉H₂₃NO₁₁
• 分子量: 441.392
• InChiKey: ZVWYQIDRLCENDG-SPOLIRPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 2,3,4-tri-O-acetyl-6-O-methyl-α-D-galactopyranoside 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以96.6%的产率得到p-nitrophenyl 6-O-methyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Monomethyl Derivatives ofP-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases

  摘要：

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.

  DOI：

  10.1080/07328300008544084
• 作为产物：
  描述：

  methyl 6-O-methyl-α-D-galactopyranoside 在 硫酸 、 溶剂黄146 、 zinc(II) chloride 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 反应 0.08h， 生成 p-nitrophenyl 2,3,4-tri-O-acetyl-6-O-methyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Monomethyl Derivatives ofP-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases

  摘要：

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.

  DOI：

  10.1080/07328300008544084