6-O-acetyl-1,5-anhydro-2,3-dideoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-erythro-hexitol | 141110-05-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-acetyl-1,5-anhydro-2,3-dideoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-erythro-hexitol
• 英文别名: [(2R,3S)-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 141110-05-6
• 化学式: C₂₂H₃₂O₁₃
• 分子量: 504.488
• InChiKey: QTUXOFOZTRCQSZ-HKOKXGGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  159.19
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-1,5-anhydro-2,3-dideoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-erythro-hexitol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 1,5-anhydro-2,3-dideoxy-4-O-β-D-galactopyranosyl-D-erythro-hexitol
  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 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 反应 72.0h， 生成 6-O-acetyl-1,5-anhydro-2,3-dideoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-erythro-hexitol
  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