2-propionylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 31826-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-propionylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: (2-propionyl-phenyl)-(tetra-O-acetyl-β-D-glucopyranoside)；(2-Propionyl-phenyl)-(tetra-O-acetyl-β-D-glucopyranosid)；1-[2-(Tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-propan-1-on；2-propanoylphenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-propanoylphenoxy)oxan-2-yl]methyl acetate
• CAS: 31826-78-5
• 化学式: C₂₃H₂₈O₁₁
• 分子量: 480.469
• InChiKey: DAYURJPHLJIOCM-XNBWIAOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2'-羟基苯丙酮 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 氢氧化钾 、 苄基三乙基氯化铵 作用下， 以 氯仿 、 水 为溶剂， 以12%的产率得到2-propionylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  摘要：

  A series of acetylated aryl beta-D-glucopyranos ides were prepared in 12-63% yields from tetra-O-acetyl-alpha-D-glycopyranosyl bromide and phenols containing acyl, formyl, and hydroxy substituents, and also from sterically hindered phenols in the two-phase system chloroform-aqueous alkali in the presence of triethylbenzylammonium chloride. Hydroxyethylated sucrose and dibenzo-18-crown-6 do not behave as phase-transfer catalysts in glycosylation of phenols.

  DOI：

  10.1023/a:1013971214679

文献信息

• Über die Synthese verschiedener o- und p-Hydroxyphenylalkyl-β-D-glucopyranoside und ihre Spaltbarkeit durch Mandel-Emulsin Mitteilung „Über Phenolglykoside”
  作者：Günther Wagner

  DOI：10.1002/ardp.19572901208

  日期：——
• ——
  作者：A. E. Pavlov、V. M. Sokolov、V. I. Zakharov

  DOI：10.1023/a:1013971214679

  日期：——

  A series of acetylated aryl beta-D-glucopyranos ides were prepared in 12-63% yields from tetra-O-acetyl-alpha-D-glycopyranosyl bromide and phenols containing acyl, formyl, and hydroxy substituents, and also from sterically hindered phenols in the two-phase system chloroform-aqueous alkali in the presence of triethylbenzylammonium chloride. Hydroxyethylated sucrose and dibenzo-18-crown-6 do not behave as phase-transfer catalysts in glycosylation of phenols.