(6S)-methyl 2,3,6-tri-O-benzyl<6-²H>-β-D-glucopyranoside | 147664-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6S)-methyl 2,3,6-tri-O-benzyl<6-²H>-β-D-glucopyranoside
• CAS: 147664-52-6
• 化学式: C₂₈H₃₂O₆
• 分子量: 465.551
• InChiKey: ZNKMCQRFDSVZAX-HTOYJLQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (6S)-methyl 2,3,6-tri-O-benzyl<6-²H>-β-D-glucopyranoside 在 palladium on activated charcoal 甲醇 、 3 A molecular sieve 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 乙酸酐 、 1,1,3,3-四甲基脲 作用下， 反应 5.5h， 生成 (6S)-methyl <6-²H>-β-lactoside
  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：

  (6S)-methyl <6-²H>-β-D-glucopyranoside 在 盐酸 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.25h， 生成 (6S)-methyl 2,3,6-tri-O-benzyl<6-²H>-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