2,3,6-tri-O-acetyl-1,5-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucitol | 141196-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6-tri-O-acetyl-1,5-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucitol
• 英文别名: [(2R,3R,4R,5S)-4,5-diacetyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 141196-68-1
• 化学式: C₂₆H₃₆O₁₇
• 分子量: 620.562
• InChiKey: YWSYRUZUWILFQU-LGJUFSBISA-N

物化性质

• 熔点：
  73-75 °C
• 沸点：
  632.9±55.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.72
• 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：
  0.73
• 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：

  2,3,6-tri-O-acetyl-1,5-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucitol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以46%的产率得到O-(β-D-galactopyranosyl)-(1->4)-1,5-anhydro-D-glucitol
  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：

  2,2',3,3',4',6,6'-七-O-乙酰基-alpha-D-乳糖基溴化物 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 2,3,6-tri-O-acetyl-1,5-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucitol
  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

文献信息

• Kessler, Horst; Wittmann, Valentin; Koeck, Matthias, Angewandte Chemie, 1992, vol. 104, # 7, p. 874 - 877
  作者：Kessler, Horst、Wittmann, Valentin、Koeck, Matthias、Kottenhahn, Matthias

  DOI：——

  日期：——