(2R,3S,4S,6R)-6-(1-Hydroxy-9,10-dimethoxy-anthracen-2-yl)-2-methyl-tetrahydro-pyran-3,4-diol | 204062-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (2R,3S,4S,6R)-6-(1-Hydroxy-9,10-dimethoxy-anthracen-2-yl)-2-methyl-tetrahydro-pyran-3,4-diol
• CAS: 204062-94-2
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.429
• InChiKey: KCAFNDYJNZCCDI-JLBIYAHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  88.38
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,6R)-6-(1-Hydroxy-9,10-dimethoxy-anthracen-2-yl)-2-methyl-tetrahydro-pyran-3,4-diol 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以36%的产率得到2-((2R,4S,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-1-hydroxy-anthraquinone
  参考文献：
  名称：

  Artificial Anthraquinone–Carbohydrate Hybrids: Design, Synthesis, DNA Binding, and Cytotoxicity

  摘要：

  DOI：

  10.1002/anie.199727481
• 作为产物：
  描述：

  methyl D-olivoside 、 9,10-Dimethoxy-1-hydroxyanthracene 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以64%的产率得到(2R,3S,4S,6R)-6-(1-Hydroxy-9,10-dimethoxy-anthracen-2-yl)-2-methyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Aryl and Allyl C-Glycosidation Methods Using Unprotected Sugars

  摘要：

  Practical and highly stereoselective aryl and allyl C-glycosidation methods using unprotected sugars as glycosyl donors have been developed. Aryl C-glycosidations of several unprotected 2-deoxy sugars with phenol and naphthol derivatives by the combined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf)-AgClO4 or TMSOTf exclusively gave the corresponding unprotected o-hydroxyaryl beta-C-glycosides which appear in many biologically attractive aryl C-glycoside antibiotics as the key subunit. On the other hand, allyl C-glycosidations of several unprotected glycals with allyltrimethylsilane by TMSOTf afforded the corresponding unprotected and 2,3-unsaturated allyl alpha-C-glycosides in high yields which are versatile synthetic intermediates for the syntheses of optically active natural products.

  DOI：

  10.1021/jo972146v