1,2,6-tri-O-acetyl-3-deoxy-4-O-(2,3,4,6-tera-O-acetyl-β-D-galactopyranosyl)-α-D-threo-hex-2-enopyranose | 141110-11-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,6-tri-O-acetyl-3-deoxy-4-O-(2,3,4,6-tera-O-acetyl-β-D-galactopyranosyl)-α-D-threo-hex-2-enopyranose
• 英文别名: [(2R,3S,6R)-5,6-diacetyloxy-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 141110-11-4
• 化学式: C₂₆H₃₄O₁₇
• 分子量: 618.546
• InChiKey: IHQVIWNZZRCZRG-JACWATPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.25
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  211.79
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  1,2,6-tri-O-acetyl-3-deoxy-4-O-(2,3,4,6-tera-O-acetyl-β-D-galactopyranosyl)-α-D-threo-hex-2-enopyranose 在 palladium on activated charcoal 氢溴酸 、 氢气 、 溶剂黄146 、 silver carbonate 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 methyl 2,6-di-O-acetyl-3-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-ribo-hexopyranoside
  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：

  溶剂黄146 、 hepta-O-acetyl-2-hydroxylactal 在 三氟化硼乙醚 作用下， 反应 1.0h， 以1.22 g的产率得到1,2,6-tri-O-acetyl-3-deoxy-4-O-(2,3,4,6-tera-O-acetyl-β-D-galactopyranosyl)-α-D-threo-hex-2-enopyranose
  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