2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxynaphthalene | 915716-22-2

• 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)-1,4-dimethoxynaphthalene
• CAS: 915716-22-2
• 化学式: C₂₆H₃₀O₁₁
• 分子量: 518.518
• InChiKey: WDMJKCSESQWZJW-PKSHOOMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  132.89
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxynaphthalene 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以97%的产率得到2-(β-D-glucopyranosyl)-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  Synthesis of β-C-glycopyranosyl-1,4-naphthoquinone derivatives and their cytotoxic activity

  摘要：

  beta-C-Glucosyl and beta-C-galactosyl-1,4-dimethoxynaphthalenes have been synthesized using a F3CCO2Ag/SnCl4 promoted Friedel-Crafts electrophilic substitution reaction. Both glycosyl acetates and methyl glycosides can be used as glycosyl donors. Further oxidation afforded the corresponding beta-C-glycosyl-1,4-naphthoquinones. The in vitro cytotoxic activity of these compounds was evaluated against the A375 cell line. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.12.017
• 作为产物：
  描述：

  1,4-二甲氧基萘 、 β-D-葡萄糖五乙酸酯 在 silver trifluoroacetate 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  Synthesis of β-C-glycopyranosyl-1,4-naphthoquinone derivatives and their cytotoxic activity

  摘要：

  beta-C-Glucosyl and beta-C-galactosyl-1,4-dimethoxynaphthalenes have been synthesized using a F3CCO2Ag/SnCl4 promoted Friedel-Crafts electrophilic substitution reaction. Both glycosyl acetates and methyl glycosides can be used as glycosyl donors. Further oxidation afforded the corresponding beta-C-glycosyl-1,4-naphthoquinones. The in vitro cytotoxic activity of these compounds was evaluated against the A375 cell line. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.12.017