3,4-dimethylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 42859-75-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dimethylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 3,4-dimethylphenyl-tetra-O-acetyl-β-D-glucopyranoside；3,4-Dimethylphenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosid
• CAS: 42859-75-6
• 化学式: C₂₂H₂₈O₁₀
• 分子量: 452.458
• InChiKey: IOOHVVLXBLLRMD-QMCAAQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  3,4-二甲基苯酚 、 β-D-葡萄糖五乙酸酯 在 磷酸 作用下， 120.0~130.0 ℃ 、4.0 kPa 条件下， 反应 2.0h， 以70%的产率得到3,4-dimethylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Novik, E. R.; Sokolov, V. M.; Studentsov, E. P., Journal of general chemistry of the USSR, 1986, p. 159 - 165

  摘要：

  DOI：

文献信息

• ——
  作者：V. M. Sokolov、V. I. Zakharov、E. P. Studentsov

  DOI：10.1023/a:1019532924135

  日期：——

  C-13 NMR spectroscopy was used to study the stereoselectivity of glycosylation of phenols with the alpha and beta anomers of penta-O-acetyl-D-glucopyranose, penta-O-trifluoroacetyl-D-glucopyranose, and 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-D-glucopyranose in the presence of boron trifluoride etherate at varied temperature, time, and catalyst amount. The boron trifluoride etherate-catalyzed reaction of penta-O-acetyl-beta-D-glucopyranose and 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-beta-D-glucopyranose with phenols occurs with a high stereocontrol to give, depending on conditions, predominantly 1,2-cis- or 1,2-trans-aryl-glycosides. This reaction can be used for preparative synthesis of the alpha- and beta-anomeric forms of glycosides of a wide range of phenols.