methyl 3,6-di-O-acetyl-2-bromo-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside | 141196-67-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,6-di-O-acetyl-2-bromo-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• CAS: 141196-67-0
• 化学式: C₂₅H₃₅BrO₁₆
• 分子量: 671.447
• InChiKey: GELKIHUDAOPKNY-YOJZCWELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  194.72
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  methyl 3,6-di-O-acetyl-2-bromo-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以38 mg的产率得到methyl 2-bromo-2-deoxy-β-lactoside
  参考文献：
  名称：

  Synthesis of Deoxy Derivatives of Lactose and their Hydrolysis by beta-Galactosidase from E. Coli.

  摘要：

  Methyl 2-deoxy-alpha-lactoside, methyl 3-deoxy-beta-lactoside, 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-glucitol and the 2-deoxy and 2,3-dideoxy derivatives of 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-glucitol have been synthesized by deoxygenation of lactose derivatives at appropriate positions. Cyclohexyl beta-D-galactopyranoside has also been synthesized. All derivatives proved to be substrates for the enzyme beta-galactosidase from E. coli, but the rate of hydrolysis of the substrate analogues was strongly dependent on the nature of the aglycone.

  DOI：

  10.3891/acta.chem.scand.46-0186
• 作为产物：
  描述：

  hexa-O-acetyl-D-lactal 、 甲醇 在 溴 、 silver(I) acetate 作用下， 反应 25.0h， 以18%的产率得到methyl 3,6-di-O-acetyl-2-bromo-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Deoxy Derivatives of Lactose and their Hydrolysis by beta-Galactosidase from E. Coli.

  摘要：

  Methyl 2-deoxy-alpha-lactoside, methyl 3-deoxy-beta-lactoside, 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-glucitol and the 2-deoxy and 2,3-dideoxy derivatives of 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-glucitol have been synthesized by deoxygenation of lactose derivatives at appropriate positions. Cyclohexyl beta-D-galactopyranoside has also been synthesized. All derivatives proved to be substrates for the enzyme beta-galactosidase from E. coli, but the rate of hydrolysis of the substrate analogues was strongly dependent on the nature of the aglycone.

  DOI：

  10.3891/acta.chem.scand.46-0186