methyl 3,4,6-tri-O-benzoyl-2-O-methyl-α-D-galactopyranoside | 280136-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-benzoyl-2-O-methyl-α-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4-dibenzoyloxy-5,6-dimethoxyoxan-2-yl]methyl benzoate
• CAS: 280136-34-7
• 化学式: C₂₉H₂₈O₉
• 分子量: 520.536
• InChiKey: PADWNQOGUFDQIK-HGQALCJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-benzoyl-2-O-methyl-α-D-galactopyranoside 在 硫酸 、 sodium methylate 、 溶剂黄146 、 zinc(II) chloride 作用下， 以 甲醇 、 乙酸酐 、 溶剂黄146 为溶剂， 反应 5.08h， 生成 p-nitrophenyl 2-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 4,6-O-benzylidene-α-D-galactopyranoside 、 苯甲酰氯 、 碘甲烷 在 palladium on activated charcoal sodium hydroxide 、 四丁基硫酸氢铵 、 盐酸 、 氢气 、 吡啶 作用下， 以 二氯甲烷 、 水 、 乙醇 为溶剂， 20.0 ℃ 、506.62 kPa 条件下， 反应 108.0h， 以55.3%的产率得到methyl 2,4,6-tri-O-benzoyl-3-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