2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(3,5-dimethoxybenzamido)hydroquinone | 1004783-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(3,5-dimethoxybenzamido)hydroquinone
• 英文别名: [(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[4-[(3,5-dimethoxybenzoyl)amino]-2,5-dihydroxyphenyl]oxan-2-yl]methyl acetate
• CAS: 1004783-21-4
• 化学式: C₂₉H₃₃NO₁₄
• 分子量: 619.579
• InChiKey: IASGLMDSJWZWNK-VFHRMQJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  202
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(3,5-dimethoxybenzamido)-1,4-benzoquinone 在 sodium dithionite 、 水 作用下， 以 氯仿 为溶剂， 反应 1.75h， 以90%的产率得到2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(3,5-dimethoxybenzamido)hydroquinone
  参考文献：
  名称：

  C-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation

  摘要：

  Reaction of C-beta-D-glycopyranosyl-1,4-dimethoxybenzenes with acetyl nitrate afforded 2-(beta-D-glycopyranosyl)-1,4-dimethoxy-5-nitrobenzenes in high yields. These were converted smoothly (reduction to amines, N-acylation, oxidation, and reduction) into the corresponding C-glycosyl-hydro(benzo)quinone derivatives, with different amide-based substituents at C-5. Reduction of the nitro compounds to amines proceeded smoothly by catalytic hydrogen transfer with HCO2NH4.

  DOI：

  10.1055/s-2007-990856

文献信息

• <i>C</i>-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation
  作者：Jean-Pierre Praly、Yun Zhang、Kaïss Aouadi、Guo-Rong Chen

  DOI：10.1055/s-2007-990856

  日期：2007.11

  Reaction of C-beta-D-glycopyranosyl-1,4-dimethoxybenzenes with acetyl nitrate afforded 2-(beta-D-glycopyranosyl)-1,4-dimethoxy-5-nitrobenzenes in high yields. These were converted smoothly (reduction to amines, N-acylation, oxidation, and reduction) into the corresponding C-glycosyl-hydro(benzo)quinone derivatives, with different amide-based substituents at C-5. Reduction of the nitro compounds to amines proceeded smoothly by catalytic hydrogen transfer with HCO2NH4.