methyl 2,3-di-O-acetyl-6-O-methylsulfonyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside | 42015-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-acetyl-6-O-methylsulfonyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• CAS: 42015-29-2
• 化学式: C₂₆H₃₈O₁₉S
• 分子量: 686.642
• InChiKey: HPMYXBZPYJEYHJ-LTSQYKSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.33
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  238.09
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-acetyl-6-O-methylsulfonyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以69%的产率得到methyl 2,3-di-O-acetyl-6-azido-6-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  The Function of the 5-Hydroxymethyl Group of Lactose in Enzymatic Hydrolysis with beta-Galactosidase from E. coli.

  摘要：

  A series of 6-substituted methyl lactoside derivatives together with methyl allolactoside and (6S)-methyl [6-H-2]lactoside have been synthesized and characterized by NMR spectroscopy. All compounds were tested as substrates for the enzyme beta-galactosidase from E. coli using progress curve kinetic methology both in single-substrate and competition experiments. The results show that the hydrolysis of methyl lactoside to a large extent takes place through an intramolecular trans-glycosidation reaction via allolactoside. Furthermore, methyl 6-amino-6-deoxy-D-glucopyranoside proved to be an inhibitor for the enzymatic hydrolysis.

  DOI：

  10.3891/acta.chem.scand.46-1114
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 吡啶 、 氢氧化钾 、 氢氟酸 、 水 、 四氯化钛 、 silver carbonate 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 5.67h， 生成 methyl 2,3-di-O-acetyl-6-O-methylsulfonyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  The Function of the 5-Hydroxymethyl Group of Lactose in Enzymatic Hydrolysis with beta-Galactosidase from E. coli.

  摘要：

  A series of 6-substituted methyl lactoside derivatives together with methyl allolactoside and (6S)-methyl [6-H-2]lactoside have been synthesized and characterized by NMR spectroscopy. All compounds were tested as substrates for the enzyme beta-galactosidase from E. coli using progress curve kinetic methology both in single-substrate and competition experiments. The results show that the hydrolysis of methyl lactoside to a large extent takes place through an intramolecular trans-glycosidation reaction via allolactoside. Furthermore, methyl 6-amino-6-deoxy-D-glucopyranoside proved to be an inhibitor for the enzymatic hydrolysis.

  DOI：

  10.3891/acta.chem.scand.46-1114